Founding Account Executive
- Remote
- $125,000
- .2-.5%
👋🏼 Who We Are
At RiskAdvisor, we’re not just building a product; we’re crafting an experience and a culture that genuinely values our customers and our team.
Our mission is simple but powerful: give independent insurance brokers the tools to work smarter, faster, and with more confidence. By streamlining, storing, and giving meaning to the data behind underwriting, we empower agencies to assess and present their value to carriers, clients, and partners.
As an insurance agency owner himself, Founder David Watson knows firsthand the challenges agents face every day. RiskAdvisor was born to make a meaningful difference in this demanding field — eliminating tedious manual processes, helping agencies grow revenue, and creating more time for the work that matters most: serving clients.
Our platform combines RiskProfiles, QuoteForms, PolicyLink, AgencyProposals, and deep integrations to simplify workflows, reduce friction, and create a single, consistent intake process across the agency. We believe that when our team thrives, so do our customers — and we’re committed to building a place where you can do your best work, enjoy the ride, and have a real impact.
💥 Why This Role Matters
This isn’t a “sit back and wait for leads” job. While you’ll have warm opportunities from our full CRM, you’ll also be responsible for filling your own pipeline, experimenting with outreach, and iterating on your pitch.
As our Founding AE, you’ll be the tip of the spear — defining our sales motion, shaping our outbound strategy, and helping us grow from SMB into mid-market and beyond. If you’re a hunter who loves to build, win, and improve with every conversation, this is your role.
🚀 Why You Should Join RiskAdvisor
Direct Impact – Work alongside the founder to shape how we sell and grow.
Real Problem, Huge Market – Independent agencies are drowning in manual workflows — we’re fixing that.
Early-Stage Equity – Be part of the growth and share in the upside.
Startup Speed – No red tape, just results.
Tools Ready to Go – HubSpot, Sales Navigator, and the tech you need to win.
🎯 What You’ll Do
Own the Full Sales Cycle – Prospect, qualify, demo, and close SMB accounts, with opportunities to expand into mid-market.
Build Pipeline – Leverage outbound, warm CRM leads, and creative outreach to stay ahead of quota.
Consultative Selling – Deliver demos that speak directly to agency pain points and workflows.
Handle Objections Like a Pro – Identify real decision drivers and move deals forward.
Share Feedback – Collaborate with product and marketing to refine our message and roadmap.
Create Playbooks – Help define what a repeatable, scalable outbound motion looks like.
🧠 What Makes You a Great Fit
2+ years outbound SDR or full-cycle AE experience in SaaS, tech, or similar.
Energized by the chase — you like finding and winning new business.
Strong communicator who can simplify complex ideas.
Resilient, resourceful, and coachable.
Organized and disciplined in your CRM usage.
Grit over pedigree — we care about results, not just your résumé.
💫 Bonus Points
Experience selling to Independent Agencies
Startup experience — comfortable with ambiguity and building from scratch.
Knowledge of insurance tech, AMS/CRM systems, or agency operations.
🎁 Benefits & Perks
Remote flexibility
Company-provided laptop
Workstation stipend
120 hours PTO per year
- Holidays & Birthday Off
🧩 What Success Looks Like
Consistently hitting and exceeding quota.
Closing deals that become long-term customers.
Building a repeatable outbound motion that fuels growth.
Becoming the AE others want to shadow.
This is a career-making role — the chance to be part of a high-growth startup from the ground up, selling a product that truly changes how an industry works. If you’re ready to own your number, shape our sales playbook, and help modernize one of the most outdated processes in insurance, we should talk.