What’s the So What? Being A Fractional Exec

What’s the So What in 100 Words?

After 6+ months as a Fractional Exec - splitting my time between Speak and WisdomAI - I've discovered that, like many things in life, every upside compared to full-time work has a counterbalancing downside. I have flexibility and variety, but miss out on deep ownership. Being part of two companies at the same time is fun, but it sets me apart from full-timers in subtle ways. I can offer more direct feedback, but with less contextual expertise. The relative quality of my work is high, but its absolute quality is lower. I'm rarely kept up late at night with work, but I sometimes miss the invigorating rush of late-night sprints. Despite these tradeoffs, the pros significantly outweigh the cons so far. I've been having a blast "Fractionaling," and it's been fun to take the time to reflect on and share my experiences.

What’s my experience as a Fractional Exec?

Since January 2024, I’ve been a fractional exec at two AI startups: spending 15-20 hours a week with Speak (an AI language learning tutor) in a GM-style role blending elements of R&D and GTM for a nascent business, and spending 10-15 hours with WisdomAI (an AI analytics company) in a GTM-focused role, focused primarily on marketing messaging and materials. Speak has ~75 employees, and WisdomAI has ~20, so both are startups, just at different stages in their growth journey.

Why Did I Choose Fractional Exec Roles?

In Q4 2023, after taking a year-long career break (see here for the write-up) following 12+ years at LinkedIn and 4+ years at 贝恩公司 beforehand, all in full-time roles, I assumed I wanted to find another LinkedIn-esque experience: that is, find a full-time role at a LinkedIn 2010-style company - a Mission-driven company that’s still private but with serious traction tackling important problems (think Figma and Notion as examples).

After turning on what I called “Career Mode” and having ~275 1-on-1 conversations between September and December, I realized that a) I wanted to go much earlier - think Seed or Series A, and b) I wanted to keep flexibility in my schedule and to “try before you buy” both the early-stage startup experience and working at specific companies of interest.

I built strong relationships with several co-founders/CXOs over repeat meetings, and?Speak?and?WisdomAI?aligned best with their near-term needs and my skills and interests. Therefore, my fractional path began.

What’s been Good and Bad about Fractional Exec-ing?

In performance reviews, we often learn that our weaknesses are our strengths taken to extremes; I’ve found the same dynamic with fractional work, where almost every upside fractional work offers has elements of a downside, too. Here's 7 So Whats so far:

(1) Fractional offers greater flexibility and variety at the expense of ownership and focus: this is the most appealing part of fractional work to me, the blend of control over my time and breadth of interests to explore. In 2024-to-date, for example, on top of both fractional roles, I’ve had the time and energy to co-found Blueprints with John Mayhall (geeking out by sharing dozens of Frameworks from our Favourite Operators) and inVest Ventures with Glenn Borok , Karen Chi , Lauri J. Moore , and others (connecting LinkedIn alumni founders with LinkedIn employee and alumni limited partner "inVestors" through a ~$2M VC Fund).

There's no scenario where I could have launched both initiatives in H1 2024 while working full-time.

The flip side is I don’t feel the same degree of capital-O Ownership in any of my 4 professional pursuits as I would if I were more myopically focused on only one. And while I'd like to think I'm above average at context switching, I've read all the research highlighting how poor we all are at it.

(2) With fractional, I get to test and learn quickly and broadly at the expense of depth: I’ve been working at two AI startups and am just beginning to ramp up with a third (winding down with WisdomAI and ramping up with a stealth company); given my prior experience was at LinkedIn - never as a true startup as we grew from ~500 employees to ~20,000 - these fractional roles are a perfect way to give me rapid breadth of exposure to early-stage companies building in the new world of GenAI. The counterbalance is that whereas I was the “glue guy” at LinkedIn - I knew almost everybody, and almost everybody knew me - just as I move from newbie to “getting it” at a company, there’s a reasonable chance I’m moving on to a new one, resetting the ramping up clock again.

(3) I can give more direct feedback, but I have less contextual expertise: fractional roles fall in the squishy area between being an insider and an outsider. This dynamic brings the pro of being more unfiltered and objective and the con that I’m prefacing my input with “I don’t have all the context, but it seems to me that…” because I don’t have the deeper expertise I’d have if working a full-time+ schedule with several years experience at the company. In addition, it means my feedback can sometimes be taken with less weight because I’m not in the day-to-day trenches like full-timers are.

(4) I don’t have the stress or impact of formal people management: fractional execs at larger companies working for more extended periods of time might formally manage people, but in my case, working at early-stage startups, formal people management hasn’t been part of my remit. This wins on the meaningful time savings spent hiring - I interview, but I'm not the hiring manager - and conducting 1-on-1s/writing reviews, etc., but it loses on the impact and satisfaction management offers. In my experience so far, I can mentor but not manage, saving me time but not giving me the opportunity to use the management skills I spent a decade+ developing and enjoying.

(5) The relative quality of my work remains high, but the absolute quality level and output volume are lower: thinking about output per hour changes how I approach work: with full-time roles, sometimes I’ve spent hours and hours polishing a product spec or presentation to make it “perfect”; that not as high ROI when I’m actually documenting where I spend every hour, especially when working at startups where the level of rigour is lower because everybody is wearing so many hats. Therefore, I’m adding good value in absolute terms, but I’d be adding more value if I ramped my hours to full-time at each company and doubled or tripled my output [which would come at the expense of flexibility and variety, the primary value props of taking a fractional path (see #1 above)].

(6) It’s easier to go to sleep and to stay asleep, which feels 80% good and 20% bad: although I’ve had the occasional late night, my time is much more blocked into chunks across the week, usually turning off at 6 or 7 pm when I head home. I have very few wakeups in the middle of the night, where my mind can’t shut down, trying to solve something. And while I'm with our kiddos, I rarely find myself dwelling on work, my brain multi-tasking behind the scenes. Put simply, it’s easier to turn work off. The flip side is that the most rewarding experiences at work are often when you’re fully turned on - with the 100% LinkedIn-appropriate connotation, of course ;) - incurring sleepless nights semi-regularly to launch something into the world alongside a cohesive team.

80% good and 20% bad is that it's easier to sleep and the professional part of my identity feels less emphasized.

(7) Finally, at least for me, the professional part of my overall identity is less emphasized, which, again, feels 80% good and 20% bad: 10-15 years ago, before our kiddos arrived, working at LinkedIn during its golden years was the central part of my waking hours and my overall identity. Post-kids, work became less central, and the transition to doing fractional work + Blueprints and inVest Ventures has made it even less central. It’s 80% good - I’m spending more time on family, friends, and fitness, for example - and 20% bad because it can be deeply meaningful to partner with colleagues and focus semi-maniacally on moving fast at work (like all Bain teams do and our early Merlin/Insights teams at LinkedIn did).

What are Quick Responses to a Range of Tapas-Style Questions?

I get peppered with A LOT of questions about fractional work from friends and colleagues. Therefore, sticking with 7s, here are 7 quick answers to some of the most common questions:

(1) What’s The Difference Between Advisory, Consulting, Fractional, And Interim?

• Advisory is what it sounds like: typically, 1/2 an hour to 2 hours per week, offering high-level advice and counsel, usually to one founder/CXO.
• Consulting is more time-consuming, anywhere from 5 to 40+ hours a week, but it still tends to be more hands-off, like advisory; the product is often a written set of recommendations rather than driving and owning major initiatives.
• Fractional has many of the elements of a full-time employee, just on a part-time, fractional basis. For example, I have an assigned desk, corporate email address, and access to Notion, Figma, Slack, and Google in a way that outside consultants wouldn’t. And I have clear responsibilities and goals.
• Interim is a role type I haven’t done (yet), but it involves doing a role full-time for a pre-defined amount of time, often a quarter or perhaps two before somebody else takes over on a full-time basis.

(2) Do I Feel Like I’m Part of the Team? About 80% “Yes”. Not to the same extent as at LinkedIn, but I also don’t feel like I’m an outsider or a second-class citizen. In addition to using all the same apps, I order the same Forkable delivery meals for communal lunches, attend and sometimes present at all the All-Hands meetings, and get invited to most social events.

(3) How Do I Work Fractionally? I’ve spent Mondays and Thursdays at Speak (in San Francisco) and Wednesdays at WisdomAI (in San Mateo), with Tuesdays and Fridays mainly for other pursuits. I learned quickly that what’s best for my personal life - ON on dedicated work days, OFF on the other days - didn’t work for my professional life because I lost too much momentum on the off days. Therefore, my best solution has been to spend ≤1 hour on my non-dedicated days (attending a meeting or two + checking in on Slack) to maintain a more consistent impact.

(4) How do I Find the Right Roles? Over the past ~12 months, I’ve defaulted “yes” to connecting with people, whether reconnecting with old friends/colleagues or meeting new folks. Taking advantage of my time flexibility, I average at least 5 and often 10 conversations weekly, roughly half in person and half virtually. Along the way, I’ve benefited from a lot of intros being made with talented founders and CXOs. My only goal going in is to be curious about what they're up to and whether I can help them. Then, over several conversations, if I’m excited about the company and they’re excited about how I could help them, perhaps we’ll partner up. Special shout-outs and thank-yous to wonderful VC friends Ansaf Kareem , Enlin Chua , and Lauri J. Moore for being connectors extraordinaire to several incredible companies and founders (including all 3 of my fractional roles).

(5) How Does My Compensation Work? I’ve structured it roughly 35-40% cash and 60-65% equity. I gathered advice from various folks, and most of the full-time consultants recommend all cash, but I’ve chosen to treat fractional roles as a much more operationally involved version of angel investing (where the larger my portfolio, the higher likelihood one company drives an outsized outcome). I only work with companies I believe in, led by founders/execs I like interpersonally, so I like aligning their results with my comp via a heavier equity focus.

(6) What New Skills Am I Learning? I’m going much deeper into creative tools than I have before. For example, as a LinkedIn PM, I sometimes commented on designers’ Figma mocks; now, I’m an intermediate approaching advanced-level Figma creator myself (I’m a much better PM and Marketer if I can create/edit mocks and designs myself). In addition, my Notion skills are 5X better, and my Webflow skills have gone from non-existent to half-decent. I even now know enough to be dangerous about using Hubspot. It’s not fair to compare the learning curve at Year 13 at LinkedIn - where I’d absorbed so many lifelong lessons over the first 12 years - with Year 1 working across 3 AI startups, but my brain just feels so much more creative and stimulated.

(7) How Long Do I Think I’ll Fractional Exec? Most important will be how two factors counterbalance each other: (1) whether I fall in love with a company (who loves me back, of course), and (2) how much I want to prioritize a wide range of pursuits like driving our kiddos to school every day and helping lead initiatives like Blueprints and inVest Ventures. I also have had the unusual opportunity to vary my roles: more GM-focused with Speak, more GTM-focused with WisdomAI, and likely more product-focused with future startups.

Overall, my current mix of flexibility, variety, and learning curve is a high bar for a full-time role to exceed.

Is Working Full-Time at One Company The Right Default Setting For Tenured Execs?

Broadening to a more philosophical question, spending 6+ months working fractionally has made me reconsider the default setting of working full-time at one company. Over the past 75 years, we’ve moved from men often working at the same company for their whole careers to a world of men and women job-hopping, freelancing, and side-hustling. And we've seen Steve Jobs and Jack Dorsey act as fractional CEOs at high-profile public companies. So, is a full-time schedule at one company the best default setting, especially for those more senior-level in their careers?

Full-time roles clearly offer the most financial stability across compensation and benefits, including health insurance. They also allow you to go deep and build true mastery in specific roles and skills. And to make a major impact with full focus. Full-time roles also provide a compelling social fabric, especially for folks in their 20s and 30s, who often move to new cities and rely on work for professional and personal relationships (Bain, for example, was well-known for its close-knit consultant classes, even resulting in 5+ marriages solely from within the San Francisco office while I was there).

I think the one full-time role value prop is much less clear for mid-career folks and beyond, especially those fortunate enough to experience a decade+ of successful runs at companies that “won big.” Financial stability and social fabric become less critical, and the ability to control your time becomes more front-and-centre. Also, having a real impact at 3 or 4 companies in a year might surpass the impact of only working at one company, especially when, after the first few years, the marginal incremental value you’re adding each year at full-time roles is decreasing.

Traditional full-time leadership roles, by definition, rarely flex down and often flex up materially; a fractional exec, on the other hand, can easily flex up and down their number of roles and hours. The bumpiness in compensation that would have been a “bug” earlier in one’s career has now become a “feature” as control of time trumps predictability of income.

For tenured execs, full time-roles are awesome - as long as they're awesome.

Overall, my biggest conclusion for mid-to-later-career-stage execs has been that full-time roles are awesome - as long as they’re awesome. Therefore, if you’re a peer or superior of mine fortunate enough to spend the past decade+ "winning" at a LinkedIn, Google, Meta, etc., and you still feel as though you "Get To" work there and love it, amazing.

However, if your job dropped below the awesome bar several years ago, and you're still there because familiarity beats uncertainty, and Big Tech pay makes you feel as though you "Have To" work there (even though you secretly know you don't), less amazing.

And if you've always wanted to work at a true startup, perhaps the fractional path is worth exploring versus playing roulette with finding your dream company through the traditional (imperfect) interviewing process.

In Closing

Finishing up, I haven’t found a lot of compelling content out there about fractional exec roles - here’s a recent Harvard Business Review piece - especially for Silicon Valley startup roles. Therefore, although 6+ months doesn’t make me an expert, if you’re interested in considering fractional exec work and my perspective can be helpful, I'm a LinkedIn DM away. And if you’re already doing fractional exec work in the startup world, I’d love to compare notes and learn together.