While reaching product market fit (PMF) is more of an art than a science, I’ve found that starting with a clear baseline on the category, customer, and core use case saves time and increases the chances of finding PMF.
Here’s a guide that I wrote back in 2021 when I was leading the Marketing team for Meta’s internal incubator, New Product Experimentation. I outlined why you want a stronger understanding of the markets you’re entering, what you should know about your market, and how product marketers and product managers can work together to build a winning go-to-market strategy.
To break entrenched habits, you need to deliver a 10X better solution. To do so, you need a clear understanding of what problems your audience cares deeply about and how they solve those problems today.
Without this understanding, you risk spending precious resources building things that aren’t likely to deliver enough value to displace the current solutions. And while you may be able to get people into the product for a first trial, it is unlikely that they’ll return and nearly impossible that they’ll tell their friends.
If you think about the products you use on a daily basis, I’m sure you can name the 10X experiences that propelled them into your daily habit. Here’s a few of mine:
*If you’re interested, this blog post shares a great outline of Spotify’s path to $20B, including their maniacal focus on audio quality to start and their decision to focus on seeding the product with music bloggers.
Effective understanding of your category means you have a strong sense of what jobs the category is hired for, what expectations consumers have of products in this category, and where there may be unmet needs. The understanding of the category (and later the ideal customer) leads to effective positioning of when, how, and why someone should pick you over another solution to their problem.
You should be able to answer:
Market/Category definition & trajectory:
Benchmark competitor: This is the competitor that is most likely to be used by your target audience. Note: the benchmark competitor is not always the market leader. It could honestly be that most people choose to do nothing or they have gotten in the habit to solve their problems with very manual solutions.
The goal is to uncover and validate that this is a high value problem that people are motivated to solve. With this understanding, you can hone in on who the product will solve this problem for first. It’s best to start with a narrow definition of the target. Find a wedge into the market. Then expand on it later.
You should be able to answer:
The core use case is that value-driving 10X better experience that differentiates you from the other products in the market. It must be noticeable and compelling enough to get your target customer over the hurdles to trial that you identified and validated in our customer understanding efforts.
You should aim to answer:
The 10X experience:
Remember, your product is your biggest GTM lever. The team should think diligently about how confident you all are in your 10X experience as well as how the product will grow before scaled releases. Then the marketing efforts can help kickstart that flywheel and even grease the tires in some places that may be slow to start.
This table seems oversimplified. But the reality is that each component has a direct parallel to product and GTM. The hard part is gathering an initial understanding and validating that against your target audience. With strong collaboration across key functions (PM, Design, UXR, DS, and PMM), you’ll be able to develop a deep understanding that fuels your product and GTM strategy.
By empowering your sales and marketing teams to work as a cohesive unit, you’re able to unlock significant efficiencies and enhancements for your business. From better leads, to a more seamless customer experience, through to higher deal conversions and improved customer satisfaction, getting sales and marketing teams to collaborate is a worthwhile pursuit.
However existing processes, structures and lack of support may be a stumbling block to getting this collaboration up and running.
A common mistake is to silo these teams from one another. An example of this would be where the sales team requests a new campaign to boost leads. Marketing does the initial research, crafts and develops the campaign, and hands over completed, sales enablement materials to the sales team. Sales then takes over and engages with potential customers, and proceeds to convert them to customers.
This cycle then repeats.
Neither team understands the other’s strategy and there is a vast abyss of shared knowledge and resources between the two. This is a mistake I initially made when taking over both the sales and marketing portfolios in a Saas enterprise. Looking back, being a conduit of information between the two crucial departments proved incredibly ineffective. We quickly realised we were missing out on opportunities and restructured things to foster collaboration.
For example, sales had brilliant insights from the field that could be integrated into integrated email campaigns to bring in a greater volume of better quality leads. And conversely marketing was quietly sitting on a wealth of data that sales could be using to pinpoint very hot leads that were likely to convert.
It was key for each team to foster a healthy understanding and respect for what the other team did. Marketing was responsible for creating awareness, which generated leads, which sales then turned them into customers. By working together, and sharing insights, Marketing could bring in better qualified leads, which Sales had a higher chance of converting.
It’s a great starting point to evaluate existing processes, structures and software to identify potential barriers to collaboration. One of the major stumbling blocks we identified was the CRM, because it was designed solely around sales efforts.
A huge project was carried out, to integrate marketing efforts into the CRM. Sales were able to quickly identify which of their prospects had engaged in a recent email campaign, and view what actions they had taken on the website. This meant they could narrow in on prospects, target the hottest leads first and craft a very tailored conversation.
TIP: When researching CRM software, analyze the integrations on offer and see how they compare to the current sales and marketing tools in your software stack. Having these integrations will foster great collaboration and knowledge sharing between the two teams.
How do you get your teams to get a fresh perspective?
The marketing team underwent sales demonstration training, so they were able to understand what it was like to sell the product. They were also required to sit on demos when members of the sales team spoke with actual prospects, and attend on-site visits with key customers.
The Sales team were required to write up their own presentation slides, outreach emails, list-build and devise campaign ideas that they thought would resonate in their regions. Overall this worked well, because not only did it give each team more exposure to another facet of the business, but it also resulted in fresh ideas and new approaches to problem solving. We improved our pre-sales materials significantly, which helped improve the quality of leads coming through. We also identified new target audiences we had previously overlooked.
TIP: Pair team members together to encourage knowledge and insight sharing, and to help build better communication across departments.
How best could we create the space to share and action deeply localized insights?
A general sales and marketing meeting was instituted every two weeks, and one of the primary aims of this was to share insights from the field. These insights would then be rolled back into campaigns. Marketing gave input and guidance on outbound sales strategy, which traditionally had been a remit of the sales team. This gave us a more cohesive approach when it came to turning a cold prospect into a happy customer.
In addition to this, there was a weekly sales and marketing meeting for each region. Here the teams got together to improve efforts on landing pages, email campaigns and social media posts. The email campaigns became highly targeted, and the messaging became deeply localized. While the product was still the same, how we spoke about the product to schools in Singapore, differed greatly to how we spoke about the product to those in North America. The results were marked improvements in open rates and click through rates, and of course sales inquiries.
Tip: Have someone take the minutes in these meetings, and rotate this responsibility each meeting. This was an invaluable resource and was a great way to ensure insights were carried through to action. It also helped new team members get up to speed quickly.
“Marketing without data is like driving with your eyes closed.” - Dan Zarrella
The two teams worked together to refine the buyer personas and map out their journeys. This collaborative effort helped marketing uncover customer pain-points they had been unaware of. It also provided a lot of real world examples that sales shared on behalf of their customers, that both teams could draw from. The insights from this shared storytelling greatly improved our messaging and even the anecdotes the sales team shared in their online, product demos.
We also mapped the customer journey from awareness to closed deal. This helped each team understand their part in the journey, and the importance of everyone telling the same story, reinforcing key messaging at each stage. Sharing this visualization was incredibly beneficial for the sales team and helped us build a more cohesive brand experience for the customer.
TIP: Facilitate regular sessions throughout the project to collaborate and debrief on mapping out the buyer personas. This will help ensure deeper alignment between the two teams, and that all key insights are shared.
What you choose to measure, you encourage. Measurement drives behavior, which then drives results. And if you’re not measuring anything, you really have no idea which way you’re moving.
KPIs for these two teams can often be miles apart, despite the functions needing to work hand in hand. By creating common KPIs, both teams are suddenly aligned towards the same goals. Good places to start are qualified leads and fit rate.The Fit rate refers to the number of conversations that your sales team needs to engage in, before finding a strong prospect. It’s the number of proposals / the number of conversations. E.g If your sales team speaks to 10 prospects before putting out a proposal, your fit rate is 10%.
Both teams focusing on increasing the fit rate, meant better leads coming into the funnel, and sales working harder on crafting tailored, meaningful conversations. Overall, the quality of incoming leads improved greatly.
Tip: Schedule a workshop between sales and marketing teams to brainstorm shared goals and KPIs that will align their efforts towards common objectives.
To help foster collaboration, evaluate your company as a whole and identify which processes, structures and in some cases even software may be stumbling blocks. Cross-train teams on the different roles, responsibilities and objectives of the two departments. The more immersive the learning can be, the better. Create spaces to foster knowledge transfer and sharing of insights, and pair up sales and marketing team members together to create deeper relationships. Each team needs an in-depth understanding of the buyer persona and the journey they take from stranger to advocate. Lastly, create common KPIs, designed to drive collaboration that both the departments can work towards.
While it may seem hard to quantitatively measure the results of these efforts initially, the long term gains are evident. Collaboration generates better quality leads, which ultimately leads to a swifter deal cycle, and a higher close rate. So get these two teams working together and supercharge your business!
As the founder of the Fractional Exec Community, I've had the privilege of engaging with hundreds of Fractional Executives from all over the globe. This has granted me a comprehensive understanding of the shifting corporate landscape and the rise of Fractional Executives. Having personally witnessed the transformative power of fractional leadership and its far-reaching benefits for both individuals and companies, I am convinced of its potential to reshape the future of work in the C-Suite.
My extensive interactions with these innovators have been instrumental in informing this article and our collective efforts to navigate the opportunities and challenges in this exciting new realm.
In this article we aim to unravel:
Several factors are accelerating the Fractional Executive trend. Firstly, the ongoing "Tech Apocalypse" has created an abundance of talent, as numerous tech companies undergo restructuring. Secondly, the shift in funding paradigms towards profitability and sustainability counters the previous growth-at-all-costs mindset; requiring senior expertise to be injected, even when budgets are tight.
Lastly, the pandemic has catalyzed two significant shifts: the acceptance of remote work, which allows executives to operate globally, and the pursuit of a healthier work-life balance by senior executives. Both these trends fuel the rise of flexible work arrangements, driving the Fractional Executive Revolution.
A Fractional Executive is a seasoned business leader who brings their skills and experience to a company on a part-time basis, typically for a specified period. Unlike consultants, they usually assume both strategic and operational responsibilities. As members of the leadership team, they hold direct accountability for key results. The primary advantage of hiring a Fractional Executive is to gain access to experienced leadership in a cost-effective, focused way.
The challenge of driving growth goes beyond crafting a well-thought-out strategy. Clayton Christensen, the father of disruptive innovation, rightly said, "In the end, strategy is nothing but good intentions unless it is implemented effectively." This statement reflects the reality of many startups that struggle to bridge the gap between strategic planning and its successful execution.
This is where Fractional Executives shine. Unlike consultants who may deliver a strategy presentation and then leave the implementation up to you, Fractional Executives are in it for the long haul. They don’t just parachute in and then disappear. They are committed partners invested in your success. I’ve seen relationships that continue on for years in a fractional capacity as well as shorter term engagements that include the hiring and training of a replacement, it really depends on what the business needs.
Fractional Executives roll up their sleeves and get into the trenches with your team. They are hands-on and involved in every aspect of execution - from designing the sales process, managing the team, writing persuasive copy, to even taking crucial sales meetings. They bring their wealth of experience and expertise to the table and work closely with your team to ensure that the strategy is successfully implemented, building the capability, resources, systems and processes required to do so.
In short, Fractional Executives help turn strategy into action, transforming good intentions into tangible results. They are the vital bridge between your strategic vision and its effective execution.
Companies employ various models to engage Fractional talent, including:
Typically, working 0.5-2.5 days per week is a common model in the Fractional Executive landscape.
Compensation for Fractional Executives varies wildly based on factors like industry, experience, company stage, and location. Fractional Exec Community members have reported rates ranging from $100-$300 per hour, $1,000-$3,500 per day, or $3,500-$20,000 per month.
As a rule of thumb, anticipate paying around 60-70% of what you'd spend on an equivalent full-time executive for 2.5 days per week. This strategy allows you to apply experience and expertise in a highly targeted and controlled manner, ensuring cost-effectiveness and flexibility.
Hiring a Fractional Executive offers several significant advantages:
Overall, Fractional Executives provide a flexible, cost-effective solution for companies seeking experienced leadership and strategic guidance.
These potential pitfalls can be mitigated through clear communication, setting realistic expectations, and careful planning.
My fractional work has actually increased my ability to perform at my day job by sharpening my skills and exposing me to a broader array of companies.
Nathan Clark, Director Sales Enablement at UpGuard, Fractional Sales Coach for B2B
I started working as a fractional VP Sales as our healthcare startup is taking longer to scale than anticipated. I absolutely love the variety of work that I see and get a massive kick out of helping early stage companies build a scaleable, repeatable sales machine.
Zachary King, Fractional VP Sales, CoFounder Mobius
I was exposed to the Fractional Model in my last Technology company and immediately fell in love with it. I want to help Startups stop making the same mistakes and I just really enjoy helping companies get their operations up to a world-class level; helping them hit the next level of their growth.
Shona Grundy, Fractional COO
We match companies with one of our vetted, Growth Connect-certified fractional CMOs. Once confirmed it’s a good fit, the fCMO will build and lead your marketing team — hiring and training internal team members, managing the marketing budget, and overseeing marketing initiatives — but without requiring the expenditures and obligations of a full-time hire. Once the team is operating at peak performance, the fractional CMO moves into a coaching or advisory role, remaining accessible for as long as you need them.
Scott Pressimone, Head Growth Connect
The Proxi Way programme, led by a fractional Chief Marketing Officer, has been designed to enable rapidly growing companies to engage with experienced business leaders at an affordable cost - not two programmes are the same as we tailor our approach to your business needs. We share aspects like Business Development across the group but each engagement has a dedicated lead Fractional CMO matched based industry and Go-to-Market experience. We call on the expertise of other Proxi CMOs when needed, for the client’s benefit.
Christelle Blanchet-Aissaoui, Fractional CMO and Co-Founder of Proxi
The growing acceptance of flexible work at a senior level is benefiting both individuals and businesses alike. Fractional Executives, with their strategic expertise and operational approach, are being deployed to tackle particular challenges or manage specific subdivisions within companies. This provides an effective way for businesses to rapidly expand, experiment, or hone their operations in new areas, with the Fractional Executive often working far less than the traditional 40+ hours per week, yet maintaining a hands-on role that exceeds that of a standard advisor.
For seasoned leaders, fractional arrangements offer a fresh model of work, one that allows them to continue exercising their leadership skills while ensuring a balance that traditional full-time roles may not permit. For the growing business, the same arrangement offers an efficient and cost-effective way to access high-level expertise.
These fractional roles can either morph into full-time executive positions over time, or they may remain as part-time commitments for several years. Irrespective of how long they last, Fractional Executives often use their newly discovered time to give back to the community, mentor startups, seek personal growth, or strike a better work-life balance.
As the landscape of corporate leadership continues to evolve, Fractional Executives are poised to play a significant role in shaping this future. If you are an experienced leader considering a fractional career or a company intrigued by the potential of engaging a Fractional Executive, we encourage you to explore this promising paradigm further.
I'm always available to share my insights, provide guidance, and facilitate connections within the Fractional Executive community. Feel free to reach out to me directly at firstname.lastname@example.org.
Whether you're an aspiring Fractional Executive or a business eager to leverage this unique expertise, let's explore the future of leadership together.
The Future is Fractional!
“But the eyes are blind. One must look with the heart.”
ANTOINE DE SAINT-EXUPÉRY
So just what is the first step in the modern job search?
Well, you could jump into action mode and do what we’ve all been trained to do: Work on your resume. Or you could fiddle around with your LinkedIn profile. Or perhaps the most mindless (and least impactful) activity: taking that stale, multipurpose resume and applying cold to every job you come across. With so many ways to browse and apply—with so many things to do—it’s no wonder that lots of searches never leave the launchpad.
But here’s the truth: All those actions won’t yield results unless they’re focused. While firing off your resume far and wide like a bazooka or clicking every “Easy Apply” button you see on LinkedIn may feel productive, it’s not. It takes a laser-guided missile to hit your target (which might be new connections, emails from a recruiter, interview callbacks, and ultimately job offers). Your first task is to get to know thyself—then find what matches are out there and get discovered for them.
So here’s a simple operating question to cut through all the analysis paralysis: What kind of job would you actually love in the first place?
If you don’t yet know the answer to that question, that’s okay. It takes time for lots of us. But until you start to develop a hypothesis about the kind of work that brings you fulfillment, every other step— building a resume, crafting a LinkedIn profile, even networking— could feel like a step through superglue. Without a clear North Star to guide you, every job search maneuver is just a shot in the dark. That’s where the Exploring step comes in.
This is an absolutely critical, soul-baring, be-truly-real-with- yourself, no-shortcuts-allowed exercise. Because when it comes to your professional brand in the digital world, getting focused— on what you really want to do next, and then on how you position yourself accordingly—is the key.
Said another way: There’s no such thing as a perfect LinkedIn profile. There is only a perfect LinkedIn profile for a specific job. What is that job for you, and for where you are right now in your career? Clarifying this will be your compass.
So to make sure you set off in the proper direction, let’s take the first step together: finding the right path for you by exploring on LinkedIn. Let’s do it in two parts: 1) understanding your options, and 2) testing your options.
Career coach Shelley Piedmont says:
“Take the first step of learning about other career options. That is the hardest one. All steps after that come much easier.”
To point your compass toward the right career path, you need to get a feel for what’s out there. Once you do, chances are you won’t have to blaze an entirely new trail. The galaxy of possibilities will be made more knowable and more manageable.
Here’s a useful case study. Jeremy used to mentor a high school student in the South Bronx named Ian. Ian had impressive clarity about his future and was dead set on becoming a criminal forensic scientist. There was only one problem: Ian hated science. Kind of a job requirement. Oops.
Upon further investigation, it turned out that Ian didn’t know any practitioners in the field. But he did watch a ton of CSI. Sure enough, he had trained his sights on the one profession that seemed cool—even though it was totally wrong for him!
Ian is no outlier. We have all done this, usually at earlier stages of our professional lives, but it’s liable to happen at other key moments of our careers, like mulling over what comes next after a graduate program, or trying to break into a new industry mid-career. We get tunnel vision on a specific path that we’ve heard about—and then start to ignore all other possibilities. And we do so at our own peril, given that just seeing a role on TV or focusing on what our friends are passionate about may block out the other careers that are indeed a better fit for us.
To avoid this trap, you must get intimately acquainted with the set of real possibilities out there. The single best way to do that is to explore the trails that others have blazed before you. Especially those with whom you already have shared work credentials or a shared affiliation—like an alma mater—who are lower-hanging fruit to connect with.
Explore the trails that others have blazed before you.
When we worked at LinkedIn, our team built a handy product called the Alumni Tool. (Sure, we’re biased, but we think it’s the best-kept secret on LinkedIn.) And even though it’s buried deep within the site, discovering it is like striking career gold: It shows the paths of every alum at virtually every school—colleges, universities, graduate programs, even many high schools—in the world.
So what makes these paths so valuable to you? And why the school-based approach to career exploration? The Alumni Tool gives you a sense of your most realistic, attainable options. After all, these alumni have been in your shoes, studied what you’ve studied, and gone on to land awesome opportunities across a variety of fields, locations, and employers. Not only that: Given your shared affiliation (Go Tigers/Aggies/Banana Slugs/Fill-In-Your-Goofy-Mascot- Here!), these contacts are also low-hanging potential referrals and informational interviewers. Their brains—and networks—are ripe for the picking.
Here’s how to start mining that alma mater career path on LinkedIn:
1. Type in your school in the search box, and choose the “School” page option.
2. Click “Alumni” at the top of the college or university’s page.
3. Welcome to the best-kept secret on LinkedIn! You now have access to all your school’s alumni on the site (i.e., those who’ve listed the school in the Education section of their profiles—all easily filterable by location, company, job, major, and connection proximity):
What to do next with this information depends on where you are in your career (e.g., a new or soon-to-be grad casting a wide net, or twenty years out with more focused requirements) and on what’s most important to your search (e.g., living in a certain geographical area, or working for a dream employer).
Here are just a few examples of the myriad ways you can purposely slice and dice this alumni data to get precisely what—and whom—you need to help you focus your job search.
Let’s say you’re a current college senior at Texas A&M University who wants to move to Austin after graduation. Select “Austin, Texas Area” from the Where they live column (if it doesn’t appear in the first set of listings, click “Add,” then search for your desired location). You have just cut down your list of 370,000+ alumni to one-tenth of that unruly number—only the 31,000+ in Austin:
And best of all, everything else in the Alumni Tool dynamically updates based on any filters you apply. So in this example, you’ll now see only the companies hiring alums in the Austin area in the Where they work column:
Okay, so what? Well, now you have a list of alumni in your desired city who are available to connect and from whom you can learn. (We’ll get into that reaching out part later in this chapter.) Just as valuable, this is also your postgraduation employer lead list. Both factors can help you get focused. It’s a custom-tailored directory of potential organizations to explore—ones in which your alumni base is already working.
Maybe you’re a new grad who’s not sure what to do with your psych degree. You’re far from alone—it turns out that, according to LinkedIn, more than a thousand Texas A&M alumni in Austin walked in your shoes and navigated that very situation. Just click the “Next” button to toggle over to the What they studied column and choose your major:
Now look at the Where they work column and behold all the most popular options at your disposal—from technology and business to academia:
Let’s say you graduated a decade ago and entered the health care sector but now want to switch into an information technology career. Choose your desired field (and perhaps also the function you want to be in) from the What they do column:
Again, notice that the other elements of this tool also update as you click into these filters. So toggle back and check out the various employers where others like you have landed jobs:
Here are a few more important notes to get the most value out of the Alumni Tool:
1. Be sure to conduct a similar search for every school you attended, in any capacity (including high schools, graduate programs, professional certificates, and even study abroad). Each new search expands your horizons even further.
2. No matter what kind of program you were in at a school, even if you didn’t complete it—a certificate, an associate’s, bachelor’s, master’s degree, or beyond—remember that the entire institution’s alumni base is also part of your network.
If you got your MBA from Texas A&M, for example, you would of course want to peruse the Alumni Tool for the Mays Business School as well as the overall Texas A&M page. But don’t skip other schools within the larger university, such as the School of Law or the School of Public Health. Whether you were part of the Texas A&M community for a semester or a seven-year PhD program, all these alumni are now at your fingertips.
Why are they so accessible? Because graduates tend to feel an affinity for their larger institutions, not just their specific pro- grams (just look at all the university logos plastered over bumper stickers, thirty years post-graduation). Omar, for example, went to UC-Berkeley’s Haas School of Business but always responds to requests he gets from anyone who’s ever been affiliated with UC-Berkeley. He loves Cal, not just Haas—and definitely not just MBAs.
3. You can custom-search far more than a location (e.g., “Austin, Texas Area” on page 68) with this tool. Don’t see a specific company, skill, or area of study in the default list of the top fifteen results? Click the “Add” button atop any of these dimensions and use the search to find the right, LinkedIn-standardized match to narrow your list:
4. For any additional search criteria that don’t fit within LinkedIn’s standardized options, you can add them using the search box at the top of the Alumni Tool:
For instance, let’s say you only want to see graduates who are in the field of Corporate Social Responsibility. Just do a search for that phrase (in quotes to capture all the words of the phrase together) and hit “Return.” Now you can see all the alumni who have that specific field anywhere on their profiles, plus updated data on where they live, work, and more:
Corporate Social Responsibility is also known as “CSR,” so you can add an “OR” operator to catch more than one phrase and widen your search.
These focused methods of finding alumni are especially help- ful at the outset of your job search. This way, no matter what’s most important to you, you’ll have a tailored list of pathways to explore. Instead of settling for just the jobs you know, you now have visibility into both a larger and more realistic set of potential jobs that you might actually, dare we say, enjoy! Just as important, you’re laying the groundwork for a network of school-affiliated people who can help surface opportunities and eventually get you in the door.
Now let’s get into how to tap the power of these career maps to build real relationships.
We’ve focused so far on examples of college and university networks. But what if you didn’t go to a four-year school? After all, two in three Americans haven’t completed a four-year degree.
Good news: The true power of LinkedIn is that it’s not some exclusive old boys’ club. Anyone can tap its data to accelerate their career. Here are two other options, no matter your educational background:
Bam! You can now explore lots of paths within your current employer (the easiest place to start) but beyond the specific job you’re doing today. Then you can also view the paths and required skills of people at other companies where you might want to work next.
You’ve just taken the critical first step: discovering an entire uni- verse of plausible professional options. This is especially something to celebrate if you’ve been feeling stuck or overwhelmed up to this point.
Now it’s time to test out those options. While it might be tempt- ing to say, “Wow, look at all these philosophy majors working at Nike; that’s the path for me,” it’s an even better idea to talk to those philosophy majors before you take the plunge.
To appreciate why, imagine this scenario: You spend the next few months hustling to land a plum job at Nike. You finally make it in. And then on your first day, your boss says: “Hey, do you mind updating all these spreadsheets by the end of the day?” Which is really too bad, given that spread- sheets are your own personal kryptonite. And the mere sight of all those blank cells makes your eyes start to bleed. And every time someone says, “Pivot Table,” you start to break out in hives. . . .
Okay, you get the picture.
To avoid this fate, you want to really dig into each possible career path and understand exactly what it entails—what would you actually do in this role, is it a good fit for your superpowers, and will it bring you meaning or misery?
The best way to do that is to talk to people who do the job—i.e., the alumni you just uncovered in the last step. After all, if you had the choice between reading about a chocolate cake in a cook- book and tasting the cake right here and now, who wouldn’t go for the real thing? The same concept applies to career exploration; there’s just no substitute for learning from real people with real expertise.
The best way to explore is to talk to the people who actually do the job.
Here’s exactly how to start up those essential conversations:
1. Once you run your initial filter(s) on the Alumni Tool to narrow down the pool of users, scroll down to see the alumni doing the very jobs in the very places you’re excited about:
2. Pick one who is doing something intriguing and click the “Connect” button. Then, be sure to also click “Add a note” (since you want to make it clear why you’re reaching out):
3. Now, here’s the most crucial part. Many people blow it by saying something like, “Hey—can you get me a job?” or “Let me tell you how awesome I am!” While you might want both things, neither is particularly appealing to an alum.
In fact, if you’re an alum yourself, you might have received at least a few messages like this. If so, you know all too well that no one wants to be so plainly sold to or used in such a transactional way.
Worry not, however, because the vast majority of alumni are happy to help out—they just want to feel good about it. They want a chance to tell their own story or steer the next generation clear of the mistakes they made. But here’s what you will almost certainly not hear: “Oh, sure, let me serve you up a job on a silver platter just because you happened to be one of the 300,000 other people who went to my school!”
So here’s an example of a note that gives the alum the spotlight instead of a sales pitch (you can find a template for this kind of outreach at the end of the chapter):
The key elements here are:
Once you’ve sent this first request, don’t stop there. You want to reach out to at least five alumni, with a goal of having three real conversations (aka “informational interviews”) per career path. Why? Well, for one thing, you’re unlikely to hear back from every alum. You also want a diverse sample of experiences to help you get focused while making a potentially foundational career decision.
For the alumni who do respond, be sure to keep track of what you learn. Make the most of each conversation by doing the following:
After each of your three (at a minimum) informational inter- views with alumni who have desirable job titles, work at companies you’re considering, or have taken career steps you want to emulate, it’s helpful to rate your level of fit. Here’s a basic rubric to evaluate what you’re learning:
Let’s look at an example: Say you just interviewed a high school math teacher, who’s told you about his days of engaging his students, helping them navigate tough challenges both at school and at home, and ultimately guiding them toward success. If you love to tell stories, have incredible interpersonal skills, and are motivated by making a difference in a young person’s life, you might rate that role a “3.” If your true love, however, is finding patterns hidden in data, your number-crunching skills are off the charts, and you’re most motivated by making sense out of lots of information, this might be a “1” for you.
Either way, your overall list will give you an average rating for each potential pathway. You can then compare the overall ratings across each of the paths to identify the one you should pursue first. Instead of stumbling out of the starting blocks like so many job seekers, you are now armed with a compass pointing you to a clear North Star.
To make sure you get the most out of your connection with fellow alumni, get ready to ask great questions. Again, you’re not pitching yourself or asking for a job—you just need the real, unvarnished truth about what the job is like.
Here’s precisely what to ask them during a phone, video, or coffee chat:
By asking these questions, you can get a sense of what it’s really like to be in their shoes—what the job feels like, how it compares to your shared experience, and what you might not expect as someone on the outside.
While many of the methods in this chapter are designed for people entering the workforce or making a significant career change, the same underlying principles apply to current employees consider- ing an internal transfer. Because a great new job—maybe even your dream job—might be just down the hall.
Often, it is.
In fact, roughly half of jobs are filled by internal candidates—it’s a whole job market of its own. So if you’re pondering (or at least open to) an internal transfer within your current workplace, you’re not wasting your time on this chapter. Much of the process is quite sim- ilar, but here are a few nuances for the purely internal job search:
Most companies will have a process for internal transfers. Understand that process. Oftentimes it will include alerting your current manager once you decide to throw in for a new job, which could potentially be a thorny situation. You must weigh the risks and benefits here, but your HR department and/or recruiting team should be a safe place to help you do so. Also, keep in mind that anyone at your company using LinkedIn’s Recruiter can’t see that you are open to new opportunities, so there’s no way to indicate to them that you want to be considered for an internal move. You can of course make this visible to all members (see page 107), but we don’t recommend that unless you’re really willing to throw caution to the wind.
We first met Andrew Kung while we were all working at LinkedIn. He was a talented recent grad who seemed to have it all: a highly selective job at a fancy-shmancy company with enough compensation to put his instant ramen–eating days behind him.
There was only one problem. Andrew felt stuck.
That’s because he was doing a type of job the world expects new grads to do (sales and customer support), not the one that he really craved and excelled at (photography). But unlike many new grads—and frankly, a lot of experienced professionals, too—Andrew wasn’t content to just defer his dreams indefinitely. Instead, he started reaching out to professional photographers through his connections on LinkedIn and realized that his dream was completely attainable.
By learning from these insiders, Andrew started to imagine an alternative future that wasn’t just pure fantasy, but one that was grounded in the reality of others’ experiences. Their stories became the paving stones for a career path that he could start to envision.
Buoyed by his career exploration, Andrew requested a transfer to LinkedIn’s New York City office. And within six months, he had networked his way into enough part-time gigs that he decided to quit the security of a big company job altogether. Pretty soon his LinkedIn Headline reflected not only his passion, but his new profession:
Within a few years, Andrew had done photography work for Beats by Dre, HBO, and Esquire—and had his work featured in the New York Times and Vogue, and on CNN.
Andrew shares this reflection on his experience: “Before LinkedIn, I always just relied on serendipity to open doors. But with LinkedIn, I realized I could engineer my own serendipity—and my own future.”
Hi FIRST NAME,
As a fellow SCHOOL alum who also majored in FIELD, I was so excited to come across your profile. I’d love to know more about how you built your impressive career—any chance you’d have a few minutes to chat next week?
Thanks for considering!
—YOUR FULL NAME
You did it! Instead of being consigned to wander the earth for all time in search of occupational fulfillment—like some kind of career zombie—you’ve just given yourself the antiserum: understanding what’s out there. And unlike the watered-down stuff that you might find on blogs and social media, you went straight to the source: real people doing the jobs you might really land soon. So give yourself a pat on the back for completing the first major step in the modern job search.
Before we move on, here’s a checklist to help make sure you’ve applied everything we just covered:
❑ Explore the career paths of alumni from your alma mater(s). Try applying the following filters to home in on people whose careers excite you:
❑ For every career path that intrigues you, reach out to at least five—yielding at least three conversations with—alumni who are in, or have done, the jobs you’re most interested in. For each informational interview, make sure to:
❑ Use these paths and informational interviews to assess your level of fit and narrow down your preferred next step.
This chapter is excerpted from our brand-new LinkedIn best-seller, Linked: Conquer LinkedIn. Get Your Dream Job. Own Your Future. (Workman/Hachette, 2022). And grab a free copy of my LinkedIn profile checklist - the only one designed by LinkedIn insiders - here.
Before joining, I tried to read what I could about Chiefs of Staff at tech companies. Ultimately, I had no playbook and was nervous/hopeful that I would do a good job. I had to take it a day at a time, and just figure it out along the way.
Though I know the experience will be different for everyone, here’s my contribution for anyone interested in what a CoS does at a seed/Series A startup, and how my role evolved over time.
I recently read that anxiety is responsible for driving us forward to succeed. During my first month at Dover I was driving a little too fast. I grasped for things to do, feeling I had a lot I needed to prove, but soon realized there was a better way for me to approach things.
I pulled the car to the side of the road and gave myself permission to lean back. I strived to listen more than I talked, and think more than I acted, telling myself to be patient, slow down, and observe.
When I joined, our CEO (Max)’s calendar was full of sales calls and first phone screens with Dover candidates. There were also random clerical things that needed to be dealt with (cancelling bills, dealing with movers to close our SF office, scheduling meetings, etc.) Dover had also not done any marketing.
My first order of business was to shift these things onto my plate. To build trust and to free time for others, I took on the administrative work alongside some of the more exciting areas like marketing that had a lot of greenfield.
At the end of my first month, I did the marketing launch for a free tool which was a nice first win. This launch outperformed some previous ones we had done and resulted in our highest traffic website day up to that point.
I closed my first sale on September 13th. By this time, my calendar had become a back-to-back block of 30 minute calls all day — split between new sales conversations and candidate screens. Max’s calendar was clearing up.
Repetition is the mother of learning. I spent all day pitching Dover to both customers and candidates, answering questions and handling objections. So I had started to build enough context to contribute to strategic conversations. My goals evolved: I had abstracted tasks away from Max, but now I wanted to be equally as effective as him.
By the end of month 2, candidates I had first rounds with were progressing into late stages, and I had the opportunity to be part of their onsites and final evaluations. In preparation for their joining, I started to build out our employee handbook.
Around the 3/4 month mark is where I started to see the magic of the CoS role. Our financial analyst, Frank joined in late October and took over contracts and other tasks related to sales Ops. Something that I had been a stop-gap for was now successfully handed off! That was cool.
Around the same time, Dover was experimenting with an “interviews product”: we had hired four people part-time to conduct first round candidate screens on behalf of our customers. Since we use our own product, I was able to start handing off internal first round phone screens to our Interviewers after conducting more than 100 calls myself! Again: where I was once focused on executing, I shifted to training others, and was free to think strategically about how to improve the process or product I’d just handed off.
Also in October, I launched another free marketing product with similar success to the previous one. We had another peak day for site traffic. In the time I had left, I wrote blog posts and got at some low hanging fruit to make our website, JDs, and employer brand stronger.
With my first 90 days down, I wanted to check in with myself. How had I done, and where was I going? This is when I decided to reach out to other Chiefs of Staff and interview them for an article. These conversations helped me define how I could be better, and what I should be striving for.
Ringing in the new year, I felt I had earned trust and started to experience flow. If my goal in previous months was to absorb our CEOs tasks, and then to be equally effective, I now felt like I was adding my own signature to things. I started to establish my own playbooks and felt the imposter syndrome fade.
Sales and Management were my two biggest responsibilities at this point. My AE workload had gone from taking up 30% of my time to 70% as inbound customers continued to pound the door. The team of 4 interviewers we had experimentally hired were working out great and customers saw value in the new product offering. So we quickly hired more people — and the growing team needed a manager. I focused my remaining time on being a stand-in for this.
At this time, People Ops was suddenly becoming more necessary. This included things like facilitating team events and bonding opportunities, orchestrating the onboarding of new team members, and later reviewing and improving those processes through feedback. I responded to thoughts and ideas as they came up.
In January, Max put a daily 1:1 on my calendar. Our working relationship got better as I got more insight into what he was doing, what I should be doing, and what was coming up. Being a remote CoS can feel wobbly — you wonder whether you’re working with complete information — so at this point, the extra time was helpful.
By February, I’d already seen my role and responsibilities evolve several times, and I could see another big change on the horizon with the possible addition of several new employees. Wanting to take stock of things, I did a sort of “audit” on my role, reviewing all I had accomplished in my core areas (Sales, Marketing, Hiring). I learned a lot about the impact of my work that had previously gone over my head.
Other Chiefs of Staff called out to me in our interviews “if you’re doing the role well, no one will know.” Chiefs of Staff therefore need to be proactive about making sure the right people know what they’re doing. So in March, I had a conversation with Max to share what I’d learned.
By April, Dover was 23 FTEs (triple since I had joined), and by May, it was time to establish our company values. I worked with our CTO to create a process for uncovering and solidifying them, then lead the workshops with our broader team. We were starting to feel like a ‘big’ company!
The contract interviewers team was growing, too. We were 12 people and counting by this point, so I appointed three Team Leads to assist with some of the ‘people’ aspects, and focused on being a liaison between the interviewers feedback and the product team building workflows for them.
In the spring, Dover supported me in going through the Coho Chief of Staff Fellowship and I was able to represent Dover at the YC GTM Expo. By this time, daily syncs with Max were no longer necessary, so we paired down to meeting once a week.
In June, we hired our first growth lead, Harry, to take over Sales. Our second growth lead, Bryant, came shortly after. This was a big deal as it meant I’d be stepping back from the day to day work of the department I’d been most focused on.
I had done short, simple trainings with other new employees as I handed off small things here and there. But this would be different. I worked closely with Harry, investing myself in ensuring he was set up for success, being an ongoing thought partner. By the time Bryant joined, Harry and I were able to share some of the onboarding responsibilities. With new sales officially off my calendar — I turned myself toward Account Management and Strategy.
In July, Mario joined as our first operations manager. Our contract interviewer team had grown to 22, and where I was previously a make-shift stop gap for managing them, Mario would be a dedicated leader for that team.
The majority of my time early Summer was spent on onboardings for Mario, Harry and Bryant. I saw my role start to transform again as in my free time, I was able to jump into what I call “strategic projects” — the random one-off side projects that are high potential for Dover and need to be proven out. I saw myself becoming the end of escalation paths, and striving to be a true stand in for our CEO on various issues/a final decider.
Over the summer, we opened an office in New York City, and announced the close of our 20M Series A.
This month marks one year at Dover, and I am very happy with how things turned out. My goal coming in was to observe and understand how a company scales from point A to point B, and to be a core part of that growth with the ability to point to things and say “I did that!”
I’m excited to see where we go from here and see what else I am able to accomplish in this role.
I mentioned early on that I did not have a playbook for being a CoS at a seed stage co. So here are a few of the things I did that I think made the difference for me.
Nick emphasized the importance of a strong business and cultural strategy, robust knowledge infrastructure, and effective communication. This helps organizations align their operations and maintain the right course for growth.
"The more time that elapses, the more you scale headcount, the more a slight change in direction renders you an order of magnitude away from your ideal destination."
Borrowing from Jeff Bezos' decision-making matrix, Nick explained the difference between big and small decisions and reversible vs irreversible decisions. They emphasized the need to think deliberately about decisions that fall into the consequential and irreversible quadrant.
We use this approach as a team at Coho too.
To make informed decisions, it's essential to maintain a hub of information across four categories: people, operations, customers, and business intelligence & finance. This will allow you to "paint an accurate picture of what is happening at the company" and make high-quality decisions.
A well-structured recommendation should accompany a strategic decision. Nick provided five components for an ideal recommendation:
1. Accurately characterize the problem
2. Use qualitative and quantitative data
3. Present scenarios, upsides, risks, and ramifications of inaction
4. Ensure the recommendation is well stress-tested
5. Balance the usage of speed, gut, and conviction with deciding carefully and rationally.
Nick emphasized that asking the right questions helps align the team, focus on the problem, and make better-informed decisions.
Draft a proposal to address the challenge or decision using the five components of a great recommendation.
a. Define the problem: Clearly describe the issue and formulate the key questions.
b. Collect and analyze data: Gather relevant qualitative and quantitative data, and consult with other leaders for insights. Could you evaluate this information to identify trends, patterns, or gaps?
c. Assess scenarios and consequences: Outline potential outcomes, upsides, and risks for each option. Consider the implications of not taking action and how the situation may evolve.
d. Test and refine the proposal: Solicit feedback from stakeholders to identify potential objections or improvements. Incorporate their input to ensure the proposal is robust and well-supported.
e. Make a balanced decision: Weigh the importance of speed, intuition, and conviction against the need for careful and rational decision-making. Aim for a timely, informed, and confident choice.
Share your proposal with your team or leadership to gather feedback and refine your recommendation.
How did the exercise help you think strategically about your organization's challenges or decisions?
What did you learn about your knowledge infrastructure?
Are there gaps or areas for improvement?
Were there any unexpected insights or areas of alignment/disagreement during the feedback process?