Founding Account Executive

Role

We’re looking for a high-velocity seller to drive net-new mid-market ARR. You’ll run end-to-end cycles for 25k–80k ACV deals (with the occasional six-figure win): prospecting into named accounts, partnering with BDRs and Marketing, running crisp discovery and tailored demos, and closing with discipline. Your job is to turn qualified interest into closed-won logos and set up land-and-expand momentum.

You’ll work directly with the founding team to sharpen our MM playbook - messaging, demos, proposals, and competitive positioning - while keeping a steady drumbeat of monthly bookings.

Responsibilities

First week

- Ramp on our ICP, platform, pricing/packaging, roadmap, and competitors.

- Learn our sales process and CRM standards; align on qualification and forecast hygiene.

- Shadow discovery, demo, and proposal calls; review recent wins/losses for patterns.

- Draft an initial plan with a named account list and vertical theses

First month

- Execute your plan: open qualified opportunities through a blend of self-sourced outbound and BDR-sourced leads.

- Run rigorous discovery and deliver tailored demos tied to measurable outcomes; document stakeholder maps and buying processes.

- Advance late-stage opportunities with mutual action plans; begin multi-threading beyond the initial champion.

- Provide tight feedback loops to founders/Product on messaging gaps, objections, and competitive intel.

First 3 months and beyond

- Maintain healthy 3x+ coverage on near-term goals with qualified pipeline; deliver predictable, accurate forecasts.

- Consistently hit monthly bookings as you ramp; drive strong win rates on well-qualified opportunities.

- Win the majority of head-to-head cycles against named competitors on ICP accounts through sharp positioning and objection handling.

- Negotiate with discipline; balance speed and control to shorten sales cycles without unnecessary discounting.

- Collaborate with AM for airtight handoffs that preserve momentum and accelerate time-to-value.

- Help refine playbooks for MM prospecting, discovery, demos, proposals, and competitive takeout motions.

About you

- Discovery and tailored demoing: you uncover pains quickly and translate them into crisp, value-led demos.

- Competitive execution: you handle objections and position effectively to win head-to-head.

- Qualification rigor: you run a structured process (MEDDICC or similar) and don’t waste cycles on bad fits.

- Negotiation and closing: you manage timelines, stakeholders, and commercial terms with control.

- Product/value fluency: you can explain the “why,” not just the “what,” to technical and business buyers.

- Coachability and continuous improvement: you test, measure, iterate; you keep clean data and strong forecast hygiene.

- Ownership mindset: you self-source pipeline when necessary, partner well with BDRs/Marketing, and run a tight process end to end.

Qualifications

- 2–5+ years of quota-carrying AE experience in B2B SaaS with consistent attainment in mid-market segments.

- Proven success closing 20k–80k ACV deals, with some six-figure wins.

- Bonus: experience selling to compliance, financial services, or regtech; early-stage startup experience.

Benefits

- 401k (100% match up to 6%)

- Destination Airbnb company work retreats 2–4 times a year

- Healthcare, dental, vision, etc.

Interview Process

1. 30 minute culture fit: In-depth assessment of your drivers, work ethic, goals, and more to determine mutual fit
2. 60 minute technical: In-depth assessment of your sales skills
3. 60 minute on-site: Meet the rest of the team
4. Reference calls