Veep.
The promotion no one tells you how to get.
To state the blindingly obvious, one reason that you might want to hitch a ride on a startup rocket ship is that it might ultimately expedite you getting to a very high level of seniority. That you can, for example, start as a humble BDR at a seed-stage llama delivery company, and, in 4 short years, wind up as the VP of Sales at Llama-Now.ai1. Indeed, just spend five seconds on LinkedIn and you’ll see plenty of 28 year old C-level executives, at least a few of whom work at companies with greater than 4 digits of revenue.
But, outside of picking the right lottery ticket, how does one actually go about getting that very exciting VP promotion?
At the close of 2016 I found myself as an ex-management consultant with a 4-year-old tech career that had really only yielded one learning: it turns out that fake money (mobile games) and fake money (crypto) are chaotic businesses with pretty short lifespans. Mostly undeterred, I figured I’d throw my hat in the ring one more time, joining the then-series C ‘DoorDash’, a last-place delivery marketplace most known for being ‘oh, so just like Uber Eats’ and very frequently confused with Jordache, the 80s denim powerhouse.
Fast forward 4 years and I was a VP, running a $1B customer experience budget, on the leadership team of a $60B public company.
Notwithstanding the rocky career route that I’d taken to get to that point - it had also included a faith-shaking stint advising America’s favorite casual dining restaurant, the inventor of the sizzling fajita! - I am sometimes asked for advice on how someone might go about ‘making VP’. So, as they were explained to me by my former DoorDash boss and mentor, here are three criteria - often never clearly articulated - you may want to seriously consider.
1. Move a number that people care about
Like everything in a well-run startup, the reward of a VP promotion is tied back to helping the company achieve its main business objective. In short, they have something you want (title, money), and you have something they want (your help in hitting the company plan).
This seems obvious, right? Hit a goal, get promoted? Well, not exactly.
With pretty surprising frequency, I see aspiring VPs overlook the “…that people care about” part. That instead of delivering on the one or two hard things necessary to move the company needle, they instead focus on hitting a range of inside baseball, vanity metrics, that might make their team feel good but do little else. Think ‘marketing qualified leads’ (MQLs) in marketing, ‘on-time shipping’ in logistics, or ‘CSAT’ in customer experience. These are all fine things for a Director, but ultimately at the VP level you’re expected to tie your accomplishments very clearly back to how they materially increased the company’s revenues or decreased its costs.
Case in point, while it didn’t hurt my own VP promotion case that I’d brought phone wait times down from 120 to 30 seconds, what was of far more importance was that I had driven such substantial efficiency improvements that the company was saving hundreds of millions of dollars a year.
So, if you’re trying to make the VP jump, make absolutely sure that you are 100% aligned with your boss, and potentially also your CEO/ CFO directly, that what you’re about to go try to accomplish really matters to them.
2. Hire a great team and then fire yourself
“The team you build is the company you build.”
Ask any founder and they’ll tell you that the number one thing that keeps them up at night is their team, and whether it’s good enough. Just go on X and see how much ink’s being spilled everyday on how to find rockstars, how to manage rockstars, and how to expeditiously fire non-rockstars.
So, if this is true, then it’s unsurprising that the path to VP involves demonstrating that you, as a company-level leader, are bringing in exceptional people to help build an exceptional company. After all, most VPs very quickly run out of capacity to do very much themselves and as such need to rely on a great team to achieve bigger and better things. So if that team’s no good, why would your founder(s) want to give you greater scope to bring in more subpar people?
On the same point, while it’s important in general that aspiring VPs hire a great team, they especially need to ensure that they’ve hired their own backfill. This is someone who is ideally already stepping in to their ‘old’ Director-level job such that they can ‘fire themselves’ and step-up into working on higher-leverage, VP-level opportunities. Or put differently, do you pass the ‘hit by a bus’ test; would your organization continue running effectively if you were unexpectedly launched off this planet?
3. Contribute to the direction of the company
The final criteria, and the one that was hardest for me to wrap my head around, is that at the VP level you’re expected to not only capably direct your function, but also make verbal and written contributions to the strategy, organization, and execution of the company overall. In my case, for example, it was no longer enough to run a high-performing CX organization on a comfortable little island. I was now, as a VP, expected to have a point of view on the merits of a new marketing program, whether to shut down an underperforming geography, or whether to hire a new external VP candidate. So, to a certain extent, being a VP is a dress rehearsal to see if you have the chops to one day, down the line, get to the C-level.
At DoorDash, as with most companies, it’s very common for irate customers to cut out customer service entirely and email their grievances to the CEO directly. The thinking - rightly - is that these will get immediate attention. And sure enough, Tony Xu, DoorDash’s co-founder, would forward me as many as 20 of these little grenades every single day.
Imagining that I was an upstanding student on the way to getting an A+, I was solving, and then responding to every ‘Tony escalation’ myself. That was until Tony shot me a note, late one Friday night.
Steve, when are you going to stop responding to these?
What I’d thought was me demonstrating my strength as an operator was actually me highlighting my weakness as a leader and VP candidate. That I must obviously have such a shallow bench that I was unable to delegate even a part of this brutal, time-sucking task.
This experience highlighted something that’s core, and yet often unsaid, about the VP promotion. It’s really not about doing more and more of what you’ve done previously, it’s an invitation to operate differently. That what made you a great Sr. Manager, Director, and Sr. Director might not necessarily get you to the top, and that a change in your scope as a leader is required to increase the scale of your impact on your company.
They deliver llamas, with llamas, with AI.