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Head of People

On Deck is where ambitious people grow, together. On Deck is where the world's top talent comes to connect.

On Deck



On Deck is where ambitious people grow, together.

On Deck is where the world's top talent comes to connect. Whatever it is our fellows want to do next, our ever-growing community and action-oriented programming will help them get there—fast. If our fellows want to learn something new to up-level their career, launch and scale big ideas, or make lifelong friends, this is the place.

Role Overview

In this role you will be the first people ops executive on our team and will make decisions that will have a significant impact on the growth and long term success of On Deck. You will work closely with our founders and executives to help us build the foundations that will enable us to continue to blitz-scale (we grew from from 6 to 60 FTE in 2020 and just hit 90). We are on the lookout for a master of the core elements of people operations who is passionate about creating an inspiring organizational culture and ensuring it can scale alongside a fully-distributed team.

You're an ideal fit for this role if you love taking things from idea to scale. You are excited by the prospect and challenge of crafting a cohesive people ops org from scratch and scaling it so we can support hundreds of ambitious team members in the coming years. You understand our business and have a strong values-alignment with how we plan to build an enduring institution while simultaneously creating one of the most powerful business engines of the decade. You will take the time to understand how our team reflects the community we serve and vice versa. You are not looking for a role where everything is figured out for you—you thrive in environments where there is ambiguity and relish the opportunity to solve problems. You understand the importance of balancing business objectives and employee experience.

Areas You'll Own:

  • Org Planning and Recruiting - You will work with our leadership and recruiting team to design our org structure and craft our hiring plans. You will build, lead and manage the Recruiting team.

  • Design and Evangelism of Company Culture and Values - We are building a company where future and former founders will find themselves in good company and where people will go to grow in their careers. You will design our culture alongside our founders by building programs that support our team and allow them to grow into the best version of themselves. You will create a brand for the On Deck culture that attracts and retains world-class candidates who are deeply passionate about our mission and values.

  • Learning and Development - We need to support our team in their career development to become world-class professionals. You will lead our L&D programs including onboarding, management and executive coaching, and ongoing educational programs for our team.

  • Performance Management and Compensation - Our team deserves guidance on what it will take to achieve their career goals. You will own the development and implementation of titling, levels, performance management and compensation across the whole company.

  • HR Operations - Our HR operations are the nuts and bolts of a well-run organization. You will own all of the systems, processes, and decisions related to these core areas of our business including payroll, benefits, and exit logistics.

Who you are:

  • You thrive in early stage environments and have significant experience building out people functions at other startups

  • You know how to manage and build great teams

  • You have exhibited the ability to understand the business objectives at the companies you've worked at so you could balance employee experience and company goals

  • You know how to work with and advise recruiting teams to create systems to hire and successfully onboard 100+ people / year

Why you might be excited:

  • We’re tackling a big problem with even bigger potential. Participants in our existing Fellowships say great things about us.

  • You’ll be able to work remotely and (mostly) set your own schedule. On Deck was a remote-first team even before COVID, so we know what makes for a great remote environment.

  • You'll have a lot of flexibility in your role, and will be able to help define our culture and operations infrastructure going forward.

  • We're backed by a who’s who of the biggest names in the venture investing world, including Village Global, Marc Andreessen, Keith Rabois, Chris Dixon, Balaji Srinivasan, Bloomberg Beta, and so many more. (Read more about our fundraise and 50-year vision here.)

Why you might *not* be excited:

  • We're ~100 people in the company now, so if you like more established companies, this role isn’t for you. You'll help create our company's culture.

  • We're an early stage startup. Projects and priorities are likely to shift.

  • Everyone on the team is extremely mission-driven, and works incredibly hard to push towards our lofty ambitions. Most people won’t be cut out for it.

  • You should be comfortable with just a dash of chaos. This is not the kind of job where you show up and we tell you exactly what to do every day.

  • On Deck is an unabashedly pro-startup, pro-tech organization. If that’s not your thing, this isn’t the place for you.


This role comes with a competitive salary, stock options, unlimited PTO with recommended minimums, and employee benefits including generous healthcare.


Our team works remotely, and we are excited about candidates globally. Please note that our team works on GMT-7 PST-friendly hours.

If you were to join On Deck, we'd want you to love it. We also know that it can be hard to tell from the outside looking in whether that would be the case for you. So, we challenged ourselves to develop an honest set of reasons someone wouldn't want to join our company. We hope it helps you make an informed decision about whether On Deck is a place you'd love to work. In summary, On Deck may not be the place for you if:

• Another company's mission gets you way more fired up.

• You want a 9-5 job.

• You do your best work in highly-structured, steady-paced, and meticulously-planned environments.

• You like finding and poking holes more than you like filling them.

• You see differences as divisions.

You can read the details of why On Deck may not be the company for you on our Non-Values page.

About this role

December 22nd, 2021

June 1st, 2021

Full Time

On Deck is hiring for this role
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About On Deck

Learn about On Deck and their company culture.

View company profile

On Deck is building a modern education institution: a platform serving the many strands of identity of ambitious people who want to change the world.

We started with the On Deck Founder Fellowship (ODF), an intensive 10-week program that helps talented, ambitious people gain the network and skills needed to build the next generation of great technology companies. We want to 10x the number of founders building world changing companies.

Then we launched the On Deck Angel Fellowship (ODA) to turn world-class operators into the next great angel investors, investing and supporting this next wave of founders.

Recently, we launched the On Deck Writer Fellowship (ODW) to help groups of enterprising writers grow their audience and hone their craft, while connecting them with a lifelong community of creative, collaborative peers.

And we’re not stopping there. To be "on deck" is to aspire to starting something new.

Start a company.
Start an angel portfolio.
Start a newsletter, podcast, media empire.
Start a new career.
*Start something*

On Deck is becoming the go-to play for ambitious people to change the world.

You can think of us almost like Silicon Valley in the Cloud, or if a digitally native Stanford for adults were built in 2020.

The On Deck Fellowship (ODF) is a 10-week virtual program where you'll have access to a network of 200+ talented founders from all over the world who are all in the early stages of working on their next company. We recently increased our support to the EMEA region too.

ODF is the perfect place to explore one or multiple ideas, meet a co-founder, and build on an early concept.

Who is it for?

Fellows typically fall into two broad categories, which we’ve taken to calling “Explorers” and “Builders.”


  • You have the skills and plan to start a company, but aren’t exactly sure yet what you want to build, or who to build it with.

  • Deep dive with experts in industries such as fintech, biotech, consumer, and participate in "request for startup" sessions with leading investors.

  • Tactical programming designed to support co-founder dating and idea validation.


  • You know what you're building, but are early in the journey, maybe you're filling out your founding team.

  • Tap the community to accelerate progress: user interviews, customer introduction, or access the collective knowledge base

  • Focus on tactical knowledge and skills – covering topics from SEO to forecasting, recruiting to fundraising.

The numbers speak for themselves...

15 Months: The first ODF cohort kicked off in June, 2019

250+ Companies: Over 250 companies founded by Fellows in the first three  cohorts

$150M Raised: Nearly $150M raised in Pre-Seed/Seed funding during ODF

Tech stack

Learn about the technology and tools that On Deck uses.

View tech stack

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