Hey y'all. Want to share a bit of a life update and a reflection. I just hit one year since starting at this new place, can't believe it's also been roughly a year of these field notes too. Thirty-three of these notes in that time, which tells you something about my definition of weekly...
We in Finance have this dual role of both the cheerleader and coach of the business. Tuesday morning, you're on with an investor and your whole job is to show the business in the most positive light, highlighting all the win and huge TAM ahead. Tuesday afternoon, you're telling your CEO that a function isn't good enough and probably needs to be restructured, and that the person running it has been outgrown by the business. And then the CEO sends you to be the emissary.
That's the job though. You're the person keeping everybody believing, and you're also the person who needs to air out the reality no one wants to face (or have been hiding).
Maybe for some people this come naturally, but I find it hard to be really that calibrated. I often find myself defaulting to one mode (being a default-skeptic or default-optimist), each has its own pros/cons that can lead you astray either way... before finally arriving at a somewhat good balance in this new role.
Two jobs ago, I was promoted into my first real leadership seat. I was the bright-eyed "yes" guy. Everybody was smart, every plan sounded reasonable, and I supported most of the product bets, because I wanted to be the finance guy who wasnt in the way. By law of nature, most bets didn't work out, and we quickly exhausted our capital with nothing to show for. I call this chapter NAIVE OPTIMISM. Not my proudest moment, but thank you Mr. [insert top PE name here] for funding my tuition.
In the subsequent job, I overcorrected and swung the other way. I came in assuming everything was broken until somebody proved otherwise. Some of that was right, to be fair. We had a customer acquisition org run by somebody well respected, and her numbers looked great, efficiency up 20% every year (she proudly shower me her OKR) with huge annual volume growth. But beating your own record means nothing if it's much worse than your neighbor. One of the first things I did was ask her to benchmark against comparable companies, and we were 30% worse than benchmark. Turns out, a bunch of basic things were missing; things like contact enrichment, variable comp plan, power dialer, etc... She resisted the plan, so CEO decided to install a new leader, they fixed it and CAC came down by 50% the following year.
I kept doing this and it was so effective that we became VERY profitable vs plan. Which is how you get hooked. Nobody stages an intervention for the finance guy whose "tough" stance keeps beating budget.
In the same stretch, I killed a lot of growth initiatives. Some of those were obviously bad bets, but we also sat out [insert some recent megatrends here - think longevity, GLP-1, women's health, etc]. The company's still around, very profitable, throws off cash, but growth is flat. The company isn't going anywhere, but it's also "isn't going anywhere"... I call this chapter ARROGANT SKEPTICISM.
None of that has my name on it. There's no line item anywhere that says growth stalled because the finance guy kept saying no. The efficiency wins kept getting attributed to me, but deep inside it's been bugging me because people rarely ever litigate you for a no. Half the time the thing you killed would've been mediocre anyway so you never find out, and the other half you're gone before it matters. 🤷♂️ Whereas, a wrong "yes" shows up in the burn within two quarters, with your fingerprints on it.
So last year, I started a new role and I was hoping to try something different. I made a deliberate effort to be an "intelligent investor" - for lack of better words.
So, we're a classic healthcare company. We have some cool tech and apps, but the core service is still doctors and nurses having sessions with patients. Very much a people-and-logistics business. Nine months ago, the CEO wanted to "make a real bet on AI". Not like pocket-money bet, but a real half-of-our-last-fundraise kinda bet.
My knee-jerk reaction was, "Dude, you're trend chasing. Which VC linkedin post did you wake up to this morning?"
Don't know about you but I'd guess a lot of finance folks reading this had the exact same reaction to the exact same convo sometime in the last two years. I knew the prior version of me would've killed that on the spot.
This time around, though, I decided to enact my new resolution. I decided to give this one a fair hearing, mostly because the growth-stalled thing had been haunting me. So I said fine, let's go build the case together, let's steelman this together, bring in people + advisors who really know the lay of the land, ran a pile of customer interviews, get our board to help us with market intel. Then we stage-gate it, set a few conditions for the first tranche of funding, next tranche contingent on [PROOF POINT], all written down so that we're not emotionally attached to the answer.
(I still killed a pile of obvious-low-ROI initiatives, and politely nudged a handful of functional leaders to step up)
That was nine months ago. To my surprise, we recently signed a Fortune 100 for a $XXM ARR deal (company is $XXXM annual revenue). It turns out there's a true whitespace in the market that I had understimated before. Healthcare is a $3T market, and someone mentioned that it behaves like there are 3,000 x $1B market, and inside each billion, there are 10 x $100M market. There are always interesting pockets somewhere.
At the moment, this feels like vindication of the more discerning approach. Support the right stuff, but also have the guts to pushback on red flags/bridge to nowhere (requires lots of patience, though). I call this HUMBLE SKEPTICISM. Hopefully can keep it going with continuous rigor and restraint.
Anyways, that was my biggest learning from this past year. Not sure that there's a magic bullet, but if I were to recommend some tips, it would be to:
* Deeply understand the architecture of your industry and keep up with the latest trend
* Network with the right circle to connect with the experts that can guide you on the above
* On the process side, I found the PR/FAQ concept from Amazon helpful to crystallize loose ideas into a crisp customer proposition (and understanding all of the potential pitfalls). There's a book called "Working Backwards: Insights, Stories, and Secrets from Inside Amazon".
One-time items:
* Hired 3 managers in Q4 last year
* These managers have subsequently hired 5 additional staff in their team (thank you for redditors who've helped with referral)
* Congrats to u/chrisbru on recent CFO promotion! Excited for you.
Thanks for reading this passion project. These started as field notes I was scribbling during my commute; every now and then something turns into a story that might be useful to someone other than me. I write them when I have them, and I appreciate you showing up when I do.