Exploring the 'Fractional' Life
You say I'm Expensive; I prefer to say I'm Valuable
This is an excerpt from an interview I did with Danny Groner, for his Substack publication for comms professionals seeking to up-level their careers, Next. Up. He had reached out because he wanted a real take on the why and the how of a fractional executive career. Is it really the best of all worlds, or is "fractional" the new code word for "too expensive" or "aged out" of the workforce? I won't speak for others, but if you are ensconced in the startup world like I am, then fractional leadership is the most viable way to contribute to companies in the earlier stages.
I asked to republish the interview because ever since I "came out" as a fractional exec, it has become one of the most common topics my network has reached out to me to talk about (that, and fundraising). While some of us are generating real value and livings out of fractional work, there remains no common language around it, how to talk about it with prospective client companies, or how to structure it. Hopefully, this interview offers some takeaways for professionals seeking more optionality in their lives.
Work is changing; we must too.
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Next. Up.: Give us a brief overview on you and your background. Where have you worked, what have you done, and what are you up to these days?
Jory: I started my career in print media, (Penguin USA, The New York Times Syndicate, Time Inc.). My dream back then was to be a novelist and essayist, and I figured I would have to pay my corporate dues to earn that autonomy. That thinking did not sustain me. The first time I quit my job to go freelance was four years into my working life, when I was 26. I would go back to numerous full-time management roles, but I believe making that first leap so early in my career set me on a path of relative confidence in my ability to adapt to independent, project-oriented work and being an entrepreneur.
My longest full-time stint was with the company I co-founded, BlogHer, a media and influencer marketing company that was acquired in 2014, now part of She Media. For most of the 10-year journey I did very little at that time other than work, sleep, travel, and think about work; while exhausting, this was also the most fulfilling work I had ever done.
I advised a few startups while building BlogHer, but doubled down after my company was acquired. Interestingly, being on “the outside” as an advisor often enabled me to more directly influence the direction of the companies I supported. Seven years and dozens of startups later I have largely been following this path, working with projects that check meaningful boxes for me, getting these companies, as I like to say, from Point A to Point B. Sometimes I work on my own, in partnership with executives from the client company; sometimes I am more embedded in the day-to-day as a fractional executive. I formalized this work into a strategic advisory I call Candor Partners.
Next. Up.: As you look back on 30 years of work, is there one common thread to your professional story? Careers are long, usually non-linear. And we sometimes only see the commonality after the fact. When you describe yourself these days to people you've just met, what do you say? If you were in a job interview, would you say something different?
There are two threads that remained throughout my career. The first one is entrepreneurism. In most of the roles I held leading up to co-founding a company, I had side hustles, writing, editing and strategy work. Later, I formally advised dozens of startups, even while I was in full-time roles, because I enjoy thinking about a plurality of missions and I enjoy the pace and vitality of teams in Build mode.
The second thread is storytelling. Perhaps because I’m a writer I define all of the business challenges I encounter as opportunities to tell a good story. Early in my career I found the business of storytelling (media) to be a lot less exciting than storytelling for world-changing ideas. The last 5-6 years of my career I’ve devoted to working in emerging tech–AR/VR, AI, blockchain/Web 3– social impact, and marketplaces. The latter because I have deep expertise there, and the former because emerging tech and movements behind ESG and DEI desperately need a compelling, ethical, logical narrative or they risk being misunderstood – or worse, abused. To me, good storytelling is not just a sales tactic or a means to a round of funding; it’s a path to positive social change.
Next. Up.: At what point in your career did you start to feel you were too expensive for companies to continue to employ you? Did it catch you by surprise? How'd you manage that period? Did you feel like you were becoming increasingly dispensable in comparison to others with radically less experience than you offered?
“Expensive” might be one way to put it. I prefer “undervalued” to describe how I was feeling. After I exited my startup I left the company after its acquisition unsure of what I wanted to do next: I had built leadership experience in business development, marketing, and strategy and encountered no roles with the same blended scope or autonomy. And I didn’t have another startup concept percolating that I was willing to go the distance for again as a founder.
I took a year to decompress and determine what I wanted to do in my next chapter. I was 42; I had two very young children and a spouse who had stayed at home with them to let me see my entrepreneurial dream through, and a mortgage–none of which I’d had when I started my entrepreneurial journey. I recall a conversation with a close friend of mine – another female founder – who shared that her 40s was the time she needed to take advantage of her “highest earning years” and get a “job-job” versus pursue the uncertain thrill of the entrepreneurial life, and I panicked. I thought to myself: Playtime is over; enough of this follow-your-bliss business and get some massive company to pay you. To do what? I wasn’t sure.
What ensued was a year of conversations with friendly executives in large companies who didn’t exactly sell me on the thrill of large company bureaucracy, and executive recruiters who told me that, despite all I had accomplished building and exiting my startup, if I was to get any role that even approximated the money I had been making, or the level of responsibility, I would need to go back in time and re-do my career. My demonstrated skills of starting a sustainable business from scratch, presenting and executing on business strategies were not as important as, say, running a multi-million-dollar P&L or managing global teams of 25+ people. In an attempt to be practical I ended up taking roles with larger companies that enabled me to check those boxes, and I learned a lot, but it was often at the expense of autonomy, creativity, and, in some egregious cases, my sense of integrity and well-being.
My big, a-ha moment was in realizing and fully acknowledging that at the top of my mountain there would not necessarily be a full-time, senior role.
My ultimate fit was playing a supporting role, sometimes a leading one, for organizations with aligned values that I could take, in any small or large way, up and to the right. And with this realization came the understanding that I would have to abandon the notion of a linear career trajectory, where my value in the market would be defined by the companies and job titles on my resume. Instead my “value” would be defined by the immediate results I could deliver for companies that matched the stage they were at. It was both a terrifying and liberating thought.
Next. Up.: I'd imagine these types of thoughts are only magnified when you're a female executive. What's it like to navigate those waters when statistically as you progress in your career you earn less than your male counterparts?
I’m sure most industries have their version of inequity toward women. I can really only speak for tech and VC-funded startups. And I have to qualify my experience by sharing that my time as a founder was Utopian, a VC-funded Themyscira, the paradise island Wonder Woman was from. We were 100% female founded, and we had a fairly straightforward time raising capital, predominantly from male VCs who appreciated what we were building. We were paid at a scale most founders in Silicon Valley were paid, not extravagantly, but at a level that was sustainable for sticking it out and building a company. And we paid our employees and contractors (we were over 80% women) on a competitive scale and on-time. In my case, my comp grew consistently with the results I achieved.
It was after exiting my company that reality hit. I received many calls from executives, new founders and VCs who wanted to “pick my brain” repetitively for no pay or equity. One startup executive wanted a product roadmap strategy and my rolodex of influencers and big brand advertisers, but he would not hire me. One founder requested that I interview her entire team and devise a marketing strategy, then backed away when I suggested that we formalize the arrangement with a contract and negotiable fee. One invited me to meet with him and his team numerous times to discuss their go-to-market strategy until I finally had to ask, “What are we doing here?” Then he demurred. One team of male founders approached me about being a founding executive, then after much discussion and an agreement, ghosted me while keeping my headshot in their fundraising deck, as my background building and exiting a company in their target market was, I’m presuming, advantageous for fundraising. One asked if I would take a leadership role in her pre-seed gig marketplace, working “more than full time” for less than what I made in my first year as a founder. When I asked if she would consider a part-time arrangement for the same comp, she asked me, “Haven’t you already made your money?”
Emotionally exhausted and genuinely confused by what felt like a year of exploitation, I lamented about all this to a close peer and female founder who had similar horror stories. “Do you honestly think,” she asked me, “that this would have happened to a man?”
Honestly thinking, I didn’t.
But I also couldn’t leave it at that. I had to take responsibility for setting a new expectation and, instead of continually feeling insulted by people I felt undervalued me, I needed to articulate upfront how I worked and expected to be compensated.
Once I had that clarity the exploitation went away.
Next. Up.: Tell us how and when you decided to become an advisor to tech companies. What does that work entail? How are you paid? How do you find companies to bring you aboard?
I’ve been advising tech companies for over 15 years. The first few approached me when I was in the midst of my journey as a startup founder, and I’ll be honest: I didn’t really know how to best add value back then, and I took whatever equity was offered. Today the calculus is way different. I do know what I can bring, and with nearly 30 companies I’ve advised, I have a better understanding of what’s reasonable compensation for the support provided.
As it turns out, while there are exploitative types who want something for nothing, there exist far more well-meaning founders who simply don’t know how to tap an advisor’s expertise in a mutually-beneficial, sustainable way. There is no playbook; I needed to write my own.
I developed a clear compensation model and value prop statement, calibrated for the stage and circumstances of the company, and I shared it with accelerators, founder groups, and VCs in my network, so that they could be better referrers.
I’ve been fortunate that companies have approached me about advising. I built a brand as a founder that has translated well in that regard. The challenge for me has been in establishing whether the companies that approach me are the right fit. There are several conditions that have to be met at the outset:
Does the company have, not just a problem I can solve, but one that I want to solve: Of the companies I’ve advised, I’ve helped most of them fundraise – turns out I’m pretty good at this. But if you want to engage me in order to lead your fundraise, forget it – this is not a competency I want to bring to the table. Any success I’ve had with fundraising comes when I’m bought into what you are building, I think you have a solid strategy toward getting it, and I know an investor that can be interested. If you don’t yet have that strategy, let’s talk about that.
Is the founder aligned with my advisory business model? I’ve taken on many equity-only roles, especially when I was in a full-time role and had no time to provide day-to-day support. But I limit those roles to no more than 20% of my time portfolio, usually less, and to only pre-funded startups, which reasonably can’t take on any paid advisors and don’t yet need that level of support. As a company grows and raises capital and/or generates revenue I don’t necessarily start charging; but typically the needs shift at this point and the company requires more time, applied strategy, and executional support. In these cases I build in a fee structure that varies on hours, scope, and fundraising stage of the company.
Is the founder aligned with how I can add value? I haven’t always gotten this one right, so now I double-down on asking questions. Startups shift constantly and founders can’t always know exactly how to leverage your expertise at every turn. But at the very least you can inquire into how they expect you to fulfill your role. You may realize expectations that are nonstarters. For instance, I recall working with a team of founders who wanted me to build a consumer go-to-market strategy for a soon-to- release web application. A few months into the role it became clear they expected me to run influencer campaigns. They had no experience in this area, and, having built a company for digital media influencers, I could understand why they expected this of me. But I didn’t agree that it made sense to lead with this strategy before the product was ready for a public launch. Had I identified this disconnect in our initial discussions I could have saved us all a lot of time, valuable early-stage funding, and myself the cognitive dissonance of acting against the best practices I knew to be effective for consumer influencer marketing.
Because fit is so critical I’m open to connecting with any founder for a 30-minute consultation. I’m glad to offer up thoughts, whether it makes sense to engage in an advisory relationship or not.
I should mention: My work is not exclusively tied to startups.
In one of my fractional roles with a large global HR tech corporation I’m supporting the strategy behind a new venture launched from within designed to drive innovation to the marketing and sales process. Another is a wholly-owned subsidiary of a long-standing organization seeking to digitally transform its model to address the next generation of corporate leaders. These are entrepreneurial ventures within more established companies.
Next. Up.: At some point, you decided to embrace the fractional title. What's it mean? Why's it a different role than being a consultant more generally? What goes into making sure these business relationships pay off? How's your work measured?
A couple of years ago I concluded that the startup hiring model was broken. I had left a company whose founders had determined their initial focus was not the right path for them, and as the marketing expert they’d hired to be their CMO, I had to agree. The founders had been so resolute about their initial plan that after closing a seed round they hired way ahead of their stage, paying me a growth-stage salary and title to match my previous experience. But after nine months of market trial and error, it was clear that the strategy and funds needed to go elsewhere.
It dawned on me that I should have explored a different kind of arrangement that, ironically, wasn’t new to me. When I was in early-stage growth at the start-up I co-founded, we’d hired an experienced executive who had worked with one of my co-founders previously. She loved our mission and had the background we needed, but we could not afford her full-time, and she was already working on a side venture she was passionate about. So we hired her part-time, with prorated equity and triggers built in for buying more of her time as funding milestones were reached. When we secured our Series B, she opted to join us as our CRO, but her role didn’t really change–she was already doing the work as a fully-integrated member of our executive team, only now on a full-time basis. She was a fractional executive; we just didn’t call it that in 2008.
Shortly after leaving that startup where I was CMO, I met another serial founder who was building a marketplace for underrepresented talent. She had built and exited three companies prior to this one and had a clear command of how to grow sustainably. Being at seed stage she knew she couldn’t hire me full-time and was open to a flexible arrangement that allowed me to take on other advisory projects. Together we crafted a scope of work for a Fractional CMO. In the months that followed I built a marketing strategy, refined existing processes, and advised on growth and exit strategy. And, after the next round of funding, I helped hire a full-time marketing leader that I support as an advisor today.
In that role I was never a “consultant” but an integral part of the executive and marketing teams.
I was invited to all company meetings with an understanding that I had limited availability and would attend the ones that were most critical. I managed a team and a budget. And I loved it! This, to me, was the best of all worlds–a way I could deliver as an operator for an early-stage company while still working on other projects and not having to worry whether my full-time status was financially hurting the company. It became my model for how I structure other fractional opportunities.
The cynicism I hear of the fractional model tends to stem from the assertion that it’s inherently ageist and exploitative – a way to get experienced, “expensive” talent on the cheap. I, and many of my fractional peers who come from startups, see it differently: I get to leverage my experience as an operator while supporting a variety of meaningful projects, all while earning potential long-term upside. I also believe that it is the best model for early- to mid-stage startups to get the expertise they need affordably. It’s a win-win for the entrepreneurially minded.
Next. Up.: If a big company approached you today with a dream offer to come on full-time, would you entertain it? Is that a path that's still open and available? What would it take to make that type of arrangement fit for you at this juncture?
Sure I’d consider it, and I have! But I’m not interested in full-time employment as a goal. I’m interested in getting companies from point A to B, and maybe to C if doing so makes financial sense and checks my boxes for fulfilling mission, best utilization of my experience, offers some learning, and enables some flexibility to pursue professional passions and time with family.
As professionally fulfilling as it was being a founder, my personal life suffered, and it stopped making sense to shortchange those in my life I justified working so hard for in the first place. I didn’t want to stress any longer about how I was going to finagle attending my kid’s teacher conference. There was a time when I was willing to have all my time “owned” by a company, and I dropped side activities that gave me joy, like networking with peers and colleagues, advising founders, writing and speaking. And then when I left a company I had to re-ignite these activities; not only is this model of working inefficient, it’s exhausting and unnecessary. It’s often this peripheral experience that adds value to a role, when I can introduce a founder to a VC I met at a networking event, or encounter a potential partner while speaking on a panel for startups. Most recently I connected two companies I was working for as a fractional and they are now gainfully partnered.
At this stage in my career, I no longer identify as a title at a company but as a unique and growing set of experiences, and an accompanying network, that can be applied to aligned companies.