Founding Account Executive

Success Matcher Recruitment; Town of Texas (WI); On-site; USD 120,000 - 230,000; Full time

Benefits offered by this job

50/50 Commission Split

Uncapped Accelerators

High Growth Startup

Job summary

Success Matcher Recruitment is representing a VC-backed startup delivering an NOI-focused operating software platform for the senior living sector. As Founding Account Executive, you will report to the Founder and help build the GTM playbook from scratch.

This full-cycle role targets $150k–$500k deals and demands a scrappy, creative approach to engage C-suite buyers. Travel to industry events is encouraged, and the position offers a strong upside with a 50/50 commission split and accelerators as

Qualifications

• 2–5 years of Full-Cycle Vertical SaaS sales experience, preferably in a VC-backed startup.
• Proven history of achieving or exceeding an annual quota of at least $850k.
• Comfortable with heavy outbound prospecting and scrappy, creative approach.
• Excellent ability to build rapport with C-suite buyers in mid-market and enterprise.

Responsibilities

• Full-Cycle Sales: manage the entire sales process from outbound prospecting to closing deals.
• Strategic Outbound: build a robust pipeline within the senior living and long-term care market.
• C-Suite Engagement: sell directly to CEOs, COOs, CFOs across 3–6 month cycles.
• GTM Evolution: collaborate with the Founder to refine messaging and market positioning.
• Travel: attend industry conferences and off-sites to build rapport and brand presence.

Skills

Full-Cycle Vertical SaaS sales

Outbound Prospecting

C-Suite Engagement

Quota Achievement

Job description

About the job Founding Account Executive

About the Role

Our client is an NOI-focused operational software platform revolutionizing the senior living industry. Their platform helps operators drive measurable revenue increases and drastic labor spend decreases. With seamless EHR integration, they serve busy portfolio leaders and frontline staff alike.

As the 14th hire and the Founding AE, you will report directly to the Founder (an early leader from Uber and Lime). You aren't just closing deals; you are building the Go-To-Market (GTM) playbook from scratch. This is a full-cycle role for an entrepreneurial spirit who loves the thrill of the hunt and the reward of building a category-defining company.

Key Responsibilities

Full-Cycle Sales: Manage the entire sales process from aggressive outbound prospecting (cold calls, email, LinkedIn) to closing $150k – $500k deals.

Strategic Outbound: Act as your own SDR to build a robust pipeline within the senior living and long-term care facility market.

C-Suite Engagement: Navigate complex sales cycles (3–6 months) by selling directly to CEOs, COOs, and CFOs.

GTM Evolution: Partner with the Founder to experiment with messaging, sales processes, and market positioning.

Travel: Attend industry conferences and company off-sites to build rapport and brand presence.

Requirements

2–5 years of Full-Cycle Vertical SaaS sales experience, preferably in a VC-backed startup.

Proven history of achieving or exceeding an annual quota of at least $850k.

You must be comfortable and proficient with heavy outbound prospecting; you thrive on being scrappy and creative.

Exceptional ability to build rapport with C-suite buyers (typically aged 50–65) in the mid-market and enterprise space.

Intellectually curious, analytical, and comfortable with the ambiguity of an early-stage startup.

Why Join?

High Impact: Direct mentorship from a Founder with a track record of scaling unicorns.

Proven Product: Incredible customer testimonials across 100+ communities and a high-caliber engineering team that ships fast.

Financial Upside: Competitive base, 50/50 commission split, and uncapped accelerators in a company with a long runway and nearing profitability.

Mission-Driven: Make a tangible difference in the quality of care and operations within the senior living sector.