VP Strategy and Chief of Staff

New York, NY
Remote âś…
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Apply before: 
Nov 19, 2022

Company Overview:

Legacy (YC S19) is a Series B startup focused on the fast-growing field of fertility and family planning. Founded at Harvard in 2018, the company has raised close to $50M from leading investors like FirstMark Capital, Bain Capital Ventures, Section 32, and celebrities like Justin Bieber. The company has raised 4 rounds of venture funding in 2.5 years. Today, Legacy is the category leader, working with major insurers, major employers, and the military, in addition to its D2C offering.

What do we do?

We are building a complete digital health hub for future parents. We aim to change the outdated view that fertility is a "women's issue" by creating an accessible, affordable product for men. This includes everything from a mail-in kit for sperm testing & sperm freezing, personalized sperm improvement products, tele-health, DNA fragmentation analysis, supplements, and more.

Job Description:

My last two Chiefs of Staff became VP Product (Seed) and COO (Series A), respectively. I am looking for someone of similar caliber for the Series B Chief of Staff. This is a VP-level position, broadly similar to what a VP Strategy would be but working even more closely with me.

In particular, I'm looking for someone who has scaled a venture-backed startup for at least 3 years, ideally beyond Series C, and now wants to be part of the leadership team at a high-impact, earlier-stage company.

I liked this description of the COS role, and am plagiarizing it wholesale:

Patrick Aylward, a vice president, and CoS at Horizon Blue Cross Blue Shield of New Jersey, breaks the job down into five roles: serving as an air traffic controller for the leader and the senior team; as an integrator connecting work streams that would otherwise remain siloed; as a communicator linking the leadership team and the broader organization; as an honest broker and truth-teller when the leader needs a wide-ranging view without turf considerations; and as a confidant without an organizational agenda. Aylward points out that “while a CEO’s other direct reports typically emphasize their own areas, a good CoS can consider the needs of the whole enterprise.”

The most sophisticated chiefs of staff also assist CEOs in thinking through and setting policies—and making sure they are implemented. They anticipate problems and are especially sensitive to issues that require diplomacy. They function as extra eyes and ears by pointing out political potholes their bosses may not recognize (especially if the bosses are new to the company). Importantly, a CoS acts with the implicit imprimatur of the CEO—something that calls for humility, maturity, and situational sensitivity.

The CoS role is decidedly different from that of the leader’s executive assistant (EA). Unlike an EA, a chief of staff works autonomously and does not handle routine correspondence or manage the leader’s day-to-day schedule. The highest-level CoS should be a full-fledged member of the senior leadership team, albeit without the rank or compensation of a C-suite officer.


  • Non-negotiable: 3+ years of high-growth, venture-backed startup experience through Series B and beyond
  • 5+ years of exceptional operational experience in startups, tech, VC, consulting and/or finance strongly preferred
  • Ideally based in New York or Boston. Preference for East Coast of US/Canada
  • MBA preferred but not required
  • Previous healthcare or consumer experience is a plus.
  • Experience with insurance is a plus (we're covered by insurers like United, Aetna, Cigna, etc.)
  • Experience with employer benefits is a plus (we're covered by employers like FB, Google, etc.)
  • Experience with the military is a plus (we work with the Navy SEALs, Green Berets, etc.)

Everything else:

  • 98th percentile energy, 2nd percentile ego. You can't afford to have ego in a job like this.
  • Entrepreneurial, scrappy, with a 'get shit done' mentality (officially we call this "bias to action"). Here I want to see examples of times you've done this before.
  • Atypically versatile. Thinks and acts like a CEO. Able to dive into many roles and do them well.
  • Willingness to challenge. This is important to me. You need to be comfortably directly challenging my opinions, assumptions, and actions, but also willing to support me if we disagree and I go in a different direction.
  • Willingness to coach and be coached. We should be learning from one another. No ego, just helping each other be our best selves.
  • Preference for candidates who have deviated from the norm. While I am impressed by candidates who did investment banking at GS, then were Baker Scholars at HBS, then joined PE/VC, this is typically not the type of person I get along best with.
  • Preference for candidates who have non-traditional/diverse backgrounds. This doesn't mean you have to fall into classic, US-centric definitions of diversity, but that you've lived a life that is different, where you've been challenged or have chosen to challenge yourself.
  • By the way, we don't necessarily have to want to "go for beers" afterward (although that would be great), but at the very least we should have an excellent working relationship and be excited to talk about different challenges and opportunities for the company!
  • I'll be interviewing candidates on a rolling basis, with an emphasis on finding the right person vs. finding someone quickly
  • Appreciation for knafeh, falafel, and hummus and/or the ability to speak Arabic is a plus!
  • Lastly - please give me a sense of who you are and why you're applying. I promise I read through everything you send.

Here's what our last 2 Chiefs of Staff had to say - and yes, we pay them, so take it with a grain of salt :)

Khaled's a first-time founder who doesn't make first-time founder mistakes. He leads with purpose, principles, and values. He's coachable: he listens, then acts. He genuinely cares about you. In my mind, the Chief of Staff role at Legacy is the opportunity of a lifetime. What Khaled's looking for in a Chief of Staff is not a direct report, but a partner. When I sat in that function, he trusted and empowered me to succeed. He's a true habibi. 15/10, would recommend.

  • Matt Wozny (VP Product)

The Chief of Staff role at Legacy was probably one of my favorite and most rewarding roles of all time. In this role, you will get direct access to a dynamic CEO and team, a front-row seat to major strategic decisions made on a daily basis, and be set up for success in every way possible by being a launching ground for something bigger and better at Legacy. Khaled is a true joy to work with - he doesn't take himself too seriously, and he also knows how to get things done like no other CEO I've ever met or known. It's an exceptional role! Come join us on this amazing journey and help make a major impact on people's lives while having a BLAST at work.

  • Sarina Richard (COO)

Why should you join us?

Look, there's lots of reasons to join any high-growth startup. "Get on a rocket ship" blah blah blah. If you're the kind of candidate we're looking for, then you already know this. Here are a few other reasons you might not already know:

We're a team of under 50 people, despite being at the Series B stage. You will be one of the first 50 employees and will profoundly impact where the company goes in the coming years.

Everyone thinks about becoming a parent. You will help couples on their journey to creating a family. You will help push society towards a fairer, more equitable place. You will be a trusted resource for men and women at the most intimate moment in their lives, including heterosexual couples, LGBTQ+ couples, and individuals who are thinking about how and when they'll want to have a family in the future.

We will invest in you like you wouldn't believe. Every single hire gets an executive coach. You'll get training for anything you need. We'll give you an unlimited 'Health & Wellness' stipend where we pay for 75% of anything you deem might improve your life (Mattresses, Pelotons, etc.) You'll have a 'buddy'. We'll set you up with a charity and match your contributions. And we will talk about your careers goals, aspirations, and feelings every single week.

(Oh - and of course you'll get the same health care, 401K, unlimited time off, and other perks that any serious company offers its team members today.)

Ultimately, we are here to win, and we believe that the best way to win is to help everyone bring their absolute best self to work. So our job is to help you be the best personal and professional version of yourself that you want to be.

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