Founding Account Executive

Letterdrop LogoLetterdrop

Date Posted

18 Jan, 2023

Salary Offered

$90 — $105 yearly

Job Type

Full Time

Experience Required

3+ years

Remote Work


Stock Options



1 available

$100k • $170k OTE • 0.1% equity • San Francisco/New York

Founding AE wanted for hazardous journey. Honor, recognition, and opportunity to become our head of sales or sales manager in event of success. Join us on our expedition!

You have prior SDR and 1 yr of AE experience under your belt at a Series A/B startup and want to try your hand at replicating that from scratch as the first sales hire. It won’t be easy. There’s no existing process, big brand, or anyone to lean on. Just you working with me, the founder, and a whole lot of moxie.

About us

Letterdrop is a YC-backed seed stage startup. We put content marketing on autopilot for B2B companies across SEO, social, and email. It’s getting harder to sell. Cold emails and LinkedIn DMs clog inboxes everywhere. Businesses need to educate customers and build trust to create sustainable lead gen. The very best companies know this. It’s a LOT of work and tooling that needs to come together to run a successful content marketing operation across ideation, project management, creation, distribution, and analytics. We automate and streamline it all so that marketers can go back to focusing on their customers instead of worrying about tactics and mundane tasks.

Very tactically, here are the top problems we tackle:

  • Webflow CMS We’re the best way to publish content to Webflow sites (we’re a Webflow launch partner on their marketplace)
  • Social Selling We can automate content distribution by your entire sales team on LinkedIn to shorten sales cycles
  • No-BS Writing That Ranks* Tools to help you write thoughtful B2B content following sales-focused frameworks and SEO-optimize your articles to rank on Google
  • Seamless Workflows Project management to manage dozens of writers and publish 100+ articles/mo
  • Analytics Automatic alerting to tell you what content needs to be updated for Google
  • Ideation Tools to help marketers understand customers better from sales calls

You’ll be working closely with me, the CEO and a VA team for prospecting. I’ve sourced and closed our first 40 customers including fast growing companies like Census, Doppler, Scribe, and CoinTracker. I was formerly a Product Manager at Google on Search and G Suite.

There’s a demo on our site and you can sign up for a trial if you want to play with the product. Just DM to cancel in 14 days.

About You

  • You’re good at listening… so good that the elderly at a nursing home would love you. You’re good at asking the right questions, extracting pain from customers, and showing them why they need to solve it ASAP (hopefully using Letterdrop).
  • You’re process-oriented. You’re going to deal with many thousands of leads and hundreds of calls. We can’t forget to follow up with folks or have our CRM look like the inside of zoo. You bring order to chaos. You’ve built and managed a sales pipeline before — finding leads, qualifying, demoing, closing... the whole shebang.
  • You’re metrics-driven. Can you work backwards from a revenue target to figure out how much outreach we need to do, disco calls we need to make, demos we need to give, in order to hit them. Missing the mark? Where should we invest to fix our pipeline?
  • You’ve got hustle and grit. This is not your mama’s AE role (though I’m sure she has an amazing sales org if she happens to be a VP Sales). This is the VERY FIRST sales hire at a seed-stage startup. Leads don’t fall in your hands. People don’t know us. We’re transitioning out of founder-led sales, but there’s no tried and true playbook. There might be bad days… in fact there are likely to be many of them. But you’re ready to scale Mt Everest, roll up your sleeves, and figure out how to sell better than Jordan Belfort. It’ll be worth it.
  • You are excited about building a sales engine. There’s very little in place today. In your eyes, you view it as a pro to learn and grow, not a con.
  • You met or exceeded quota at your previous job and your manager says something along the lines of “I’ll be working for you one day”.

Who is this for?

  • You want to cut your teeth as the first sales hire on a small team.
  • You’re not one for defined roles. You can cold call, build pipeline, and are persistent without being pushy. You’re creative and flexible to try anything and everything to book calls with our ICP. You can figure out how to navigate an org and get the right people into the conversation, tell them exactly what they need to hear in order to close a deal.
  • You’re excited to step up and grow into a bigger role. All sales to date has been founder-led. You’ll be taking on ownership of the entire sales pipeline from prospecting to closing. In 6 months, if things are going well, you can help me hire our first SDRs, other AEs, and you’ll be first in line when we’re looking to build out our sales leadership team.

Who is this not a fit for?

  • You can’t work hard right now. If you have other priorities outside of work, being the first sales hire at a startup is probably not the right move.
  • You need a traditional environment and structure. I’m a technical founder who has had to learn how to sell. We’re still figuring out our revenue org. I don’t have all the answers. You’re excited to figure it out with me.
  • You’re not excited about our customer. The nice thing about Letterdrop is you’re selling to marketing teams and we impact pipeline. The problems we solve are very relevant to your job. You’ll have way more fun if you’re passionate about helping marketing and revenue orgs.

If the above make you even more excited, great! If it’s not a fit, that’s cool too — good to get it out of the way early.

What will you do?

  • Prospecting customers using LinkedIn, Apollo, Job Boards, BuiltWith, marketing communities and other tools. You can leverage our offshore team for data collection
  • Become a LinkedIn influencer to bring leads to you - you can leverage Letterdrop
  • Cold calling - it’s surprisingly effective if you’re confident
  • Reach out to prospects through LinkedIn and cold email with thoughtful and succinct personalized emails
  • Qualify opportunities and figure out if we can actually help a company or if they’re too early/not a fit. Be decisive so you can spend time on better opportunities
  • Identify the biggest baddest pain point a lead has - we can’t sell to someone who doesn’t have any pain
  • Run disco and demo process with the right people in the room. We typically deal with 2-5 stakeholders
  • Move heaven and earth to make a deal close
  • Hit monthly quotas
  • Work directly with me, the CEO, to shepherd deals from first touch to close
  • Note that this is the first sales hire. Commission structure will change after first year as we learn


  • Located in San Francisco Bay Area (preferred and 2-3 days/week in office) or New York
  • 1-2 yrs of experience as an AE at a Series A/B company. And prior experience as an SDR. You need to be better than me at generating pipeline and closing.
  • Experience selling to revenue teams: Marketing, Sales, RevOps
  • Experience working with mid-market companies: Series A and above, under 1000 employees, low to mid 5 figure contracts
  • A genuine interest in using content to sell - you’re ready to become a LinkedIn influencer
  • Bachelor’s degree (preferred, not required)

About Letterdrop

Letterdrop Logo

B2B content operations on auto-pilot

Company Size: 6 - 10 People
Year Founded: 2020
Country: United States

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