Career Coach


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Career Coach / Remote / Talent Marketplaces / Full-TimeTL;DR: On Deck is hiring a startup-centric Career Coach to empower mid and senior-level talent to navigate and advance their careers in the startup space. Critical to this role is deep experience and expertise in career-building at early-stage startups, including navigating startup compensation.
About On DeckOn Deck is a global community where ambitious, talented people start and scale companies and invest in their careers among a cohort of their peers.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. You can think of us almost like Silicon Valley in the Cloud. To be "on deck" is to aspire to start something new.Read our Wall of Love and our Alumni Case Studies to get a sense of why people love being part of this community.
Role OverviewIn early 2022, On Deck is launching Career Center, a new business unit to support thousands of fellows (and soon, the public) with 1:1 and small group coaching to help build their careers at startups. In addition to serving our broad network of 8,000+ Fellows (and counting!), Career Center will place special emphasis on serving Fellows in the On Deck First 50 program, which caters to job-seekers in the startup space.
We are hiring our first 1-2 Career Coaches who will bring our vision for this service to life. You will provide direct career coaching to ambitious mid and senior-level professionals looking to advance their startup careers. You'll help us figure out what to offer, how to make it awesome, and how to scale it to thousands of clients.

Who you are:

  • Must-have: You have strong experience coaching professionals in the early-stage startup space (pre-Seed to Series B). To build credibility with our clients, you will need to be deeply familiar with the startup job search process, and how that compares to traditional searches. Expert knowledge of early-stage startup compensation packages is highly important.
  • You love, love, love helping people navigate the exciting, confusing, frustrating, wonderful journey that is building a career. You have enough legible experience doing this work that even seasoned startup players will trust you to guide their career transitions.
  • You have high EQ and are able to quickly establish trust and credibility with clients; you are thoughtful and varied with your approaches in navigating a client's career path; you are a skilled communicator and collaborator.
  • You thrive in a fast-paced, scrappy, often chaotic and ambiguous environment.
  • Your coaching clients, colleagues, and friends describe you as a "wonderful human."
  • Bonus points if: You have a background in recruiting or have been involved on the hiring side for a large number of candidates.
  • You have experience in executive coaching, especially for CxOs at startups. (If you have significant experience here, know that we have another role cooking that may be a better fit.)
  • You bring a unique background, identity, perspective, or life experience that adds to the diversity of the Career Center team.

What you will do:

  • Provide direct career coaching to professionals in the startup ecosystem. This will include 1:1 coaching (one-time and ongoing), themed coaching packages (e.g. Developing Your Job Search Toolkit), large-group presentations or workshops, and small group facilitated coaching.
  • Offer guidance on startup compensation and negotiation, especially at the offer stage.
  • Develop one-to-many self-serve resources, such as interview prep guides, self-discovery activities, and resume checklists.
  • Design and launch new experimental offerings based on client feedback and your ideas.
  • Share in a culture of feedback and actively participate in a community of coaches continuing to hone their skills and add to their coaching knowledge.
  • ... and whatever else will create value for Career Center clients. We pride ourselves on a culture of experimentation and constantly look for opportunities to build the next great thing. Help us build the nascent Career Center in whatever way you are most qualified and interested.
  • Please note that we expect to hire many more Career Coaches in 2022 as we grow this business. Beginning in late Q1 2022, we will be looking for career coach specialists, contract coaches, and non-startup-centric coaching generalists. We may also be open to hiring On Deck Fellows with non-traditional coaching or mentoring experience. But for our first hires, we are focused on the profile described above. 

Why you might be excited about On Deck:

  • 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 what our operations infrastructure looks like going forward.
  • We're backed by a who’s who of the biggest names in the venture investing world, including Village Global, Keith Rabois, Balaji Srinivasan, Bloomberg Beta, and so many more. (Read more about our Series A in this memo)

Why you might *not* be excited about On Deck:

  • We are a young company with about 250 people, 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. If you're looking to clock out after your 9-to-5, this place is not for you. (But know that we also don't work 80-hour weeks, and we don't want you to burn out.)
  • 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.
Additional details about working at On Deck:Please note this role is only open to candidates that are legally authorized to work where they reside. Due to the remote nature of the role, On Deck does not currently sponsor candidates for visas or work authorizations/permits and does not currently support the transfer of visas or work authorizations/permits from prior employers to On Deck.
CompensationThis full-time role comes with a competitive salary, stock options, unlimited PTO, health and wellness stipend, SaaS product stipend, Macbook, and employee benefits including healthcare.
LocationOur team works remotely, and we are excited about candidates globally.  Please note that our team works on GMT-7 PST-friendly hours, so your location will affect your work hours, which may be difficult from APAC.
Equal Opportunity EmployerOn Deck is an equal opportunity employer dedicated to building an inclusive and diverse workforce. All employment is decided on the basis of qualifications, merit, and business need. We strongly encourage applications who are members of underrepresented communities to apply.#LI-remote
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 believe that something has to be exclusive for it to be cool You can read the details of why On Deck may not be the company for you on our Non-Values page.
Job region(s): Worldwide/Anywhere
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