Sales Expert (Part-Time, Contract to Hire)

About First Round's Founder Success Team At First Round, we invest in founders who possess not just strengths, but areas of true genius, whether it’s technical skill, product judgement, industry expertise, or a deep understanding of their customer’s pain point. But on the other side of every spike in talent are a few areas that are still underdeveloped, parts of the business where a founder doesn't have the skills and expertise — yet. Simply put, there are many gaps that have yet to be closed when you’re only a 3-person startup. On the path to building a company of consequence, the very best founders are able to level up, both in terms of their own capabilities (by developing new muscles) and in the team around the table (by bringing in complementary talent). That’s where our Founder Success team comes in, during the pivotal early years of company building. We fill in where we can until there's genius up and down the org chart, closing gaps around existing strengths while helping in the key growth areas on the transition from founder to founder & CEO. This might involve teaching a technical founder how to sell and take their product to market, or guiding them through making their first key hires. About the Role *This role begins as a part-time contract position, with the possibility of transitioning to full-time for the right candidate. You will need to be San Francisco or New York-based (3 days/week in-office). This is a founder-facing, in-the-trenches role supporting our founders in landing their first few dozen customers. This isn’t armchair advising; it’s getting your hands dirty alongside (largely technical, largely B2B) founders. You’ll be both a strategist and an operator. Here’s what we mean by that: As a strategist, you might recommend whether a company should go with a value-based pricing strategy or a competitive pricing strategy based on their business, competition, product etc. As an operator, you’ll help them actually build their value-based model in Excel. As a strategist, you might teach a founder best practices in running discovery calls. As an operator, you might listen to 5 of their calls and provide tactical feedback on a live call. As a strategist, you might help a founder prepare for a big pilot wrap up call by giving them a recommended agenda. As an operator, you might build their pilot structure from the ground up in Notion. We’ve been supporting founders in this way for many years. With demand at an all-time high, we’re looking for additional experts to pinch-hit as early GTM hires until our companies hire one of their own. Your core responsibilities will include: Build the foundation : Figure out the early sales process steps, build enablement materials, test out pricing models etc. Ride along on big opportunities: Help founders work big opportunities step by step to close by prepping with them, listen to calls and providing feedback and sometimes joining calls Run fast paced engagements : Lead end-to-end projects through live working sessions and async follow-up work to unblock founders and help them accelerate sales Typical projects: Listen to founder’s sales calls and provide tactical feedback Help founders design their sales motion – their sales processes, pilot programs, pricing models, commission plans etc. Help founders build enablement materials – decks, pilot documents, proposals, business cases etc. Ride along on important sales calls (and follow ups) with founders Interview founding SDR/AE candidates to help founders find the perfect fit for their early hires Required Experience At least 5 years in a Founding GTM / Founding AE / Founding Head of Sales role At least 5 years of new business quota carrying experience Have worked in at least 2 different startups that achieved several million in ARR (you’ve “seen the movie” more than once) Experience closing deals of varying sizes, but primarily $25K - $300K ACV You could be a great Sales Expert In Residence at First Round if you: You have a minimum of 5 years of experience supporting early stage ( You’ve done the zero to one thing, working super closely with pre seed or seed stage companies on early sales strategy and execution across industries, buyer personas, ACVs and GTM motions. You have a lot of empathy for and experience with working with early stage founding teams. You have a services mindset . Whether you were in house and/or had your own freelance/advisory gigs, you know how to engage, manage, and transition multiple clients (founders) at a time. You love to wow your clients by anticipating their needs and going above and beyond with creative ways to support their goals. You’re amazing at calendar juggling and code switching between wildly different contexts. You’re incredible at learning fast and context switching. You could be working with 2-3 founders at the same time. You can get up to speed quickly on all of them and juggle that amount of context in your brain. This is very different from working in-house at a startup with one founder and one GTM motion. You’re prescriptive . You understand sales isn’t a one-size-fits-all function. You’ve seen enough variety in your career to be able to deeply digest a company’s ICP/persona/competition/market and recommend sales tactics that deliver results. In essence, you know how to be prescriptive (not just copy an old playbook). You’re scrappy and fast . You always manage to just figure stuff out, even with limited support or budget. And nothing is too small for you to do. You love the idea of taking a problem or goal and coming up with new ways to tackle that problem or achieve that goal. You embody extreme ownership . You own your job through and through. No one has to tell you the next step to take or the next email to write. You’re extremely autonomous and are a driver, pushing things forward and proactively unblocking barriers on the way to the goal. You are obsessed with details and process. You’ll likely be supporting a handful of companies at one time. This requires an exceptional level of organization and detail orientation. This looks like you having detailed notes on every engagement, using Notion like a pro, having amazing CRM hygiene. You remember the little things and never let a ball drop. Details: Up to 15 hours per week (weeks may vary from 0–15 hrs) San Francisco or New York-based (3 days/week in-office) 3-month contract with potential extension or full time conversion, if mutually agreed Salary / Hourly Rate : Dependent on experience

{
  "content_hash": "6980c2e6519e0adfc15536ec68c3467689d6472e4fa20d6ddc6b1f4bdc5cbfa1",
  "source_hash": "6f1b5660db3a1c86f2f6fca6efbccaca3a8f28e1a4850700c557df36c854b3f2",
  "last_changed_at": "2026-05-29T05:23:26.342Z",
  "active_status": "active"
}

{
  "language": "en",
  "location": {
    "raw": "San Francisco, CA",
    "city": "San Francisco",
    "region": "CA",
    "country": "United States",
    "is_remote": false,
    "confidence": 0.9
  },
  "salary_max": null,
  "salary_min": null,
  "inferred_at": "2026-06-06T19:41:32.584Z",
  "launch_scope": {
    "reason": "english_us_canada",
    "included": true,
    "language": "en",
    "location": {
      "raw": "San Francisco, CA",
      "city": "San Francisco",
      "region": "CA",
      "country": "United States",
      "is_remote": false,
      "confidence": 0.9
    },
    "countries": [
      "United States"
    ]
  },
  "remote_policy": "hybrid",
  "salary_period": null,
  "workplace_type": "hybrid",
  "salary_currency": null
}

{}

{
  "id": "f2568259-9b0a-4622-a52d-4f6f58bbf09f",
  "team": "Operating Team",
  "title": "Sales Expert (Part-Time, Contract to Hire)",
  "jobUrl": "https://jobs.ashbyhq.com/firstround/f2568259-9b0a-4622-a52d-4f6f58bbf09f",
  "address": null,
  "applyUrl": "https://jobs.ashbyhq.com/firstround/f2568259-9b0a-4622-a52d-4f6f58bbf09f/application",
  "isListed": true,
  "isRemote": false,
  "location": "San Francisco, CA",
  "updatedAt": null,
  "apiVersion": "ashby-non-user-graphql-v1",
  "department": "Operating Team",
  "publishedAt": null,
  "workplaceType": "Hybrid",
  "employmentType": "FullTime",
  "secondaryLocations": [
    {
      "location": "New York, NY"
    }
  ]
}