What You’ll Do
1. Own the Full Sales Cycle
- Run qualification → discovery → solution design → demo → proposal → close
- Articulate financial ROI clearly and credibly: margins, interchange, cost savings, operational lift
- Multi-thread across operational, finance, and leadership stakeholders
2. Build the Early GTM Motion
- Create the AE playbook: outreach sequences, objection handling, demo frameworks
- Help architect our CRM structure, pipeline methodology, and deal stages
- Partner with Marketing to refine ICP, messaging, and lead scoring
3. Be the Voice of the Customer
- Funnel real customer feedback directly into product, ops, and leadership teams
- Influence feature prioritization and onboarding workflows
- Identify repeatable patterns that inform GTM scaling
4. Drive Pipeline & Growth
- Convert a mix of inbound and self-sourced pipeline
- Build early outbound campaigns into high-value verticals
- Establish channel/partner strategies (ISVs, processors, VARs, MSPs, accountants, etc.)
Who You Are
- Fintech or POS sales experience is strongly preferred (Toast, Lightspeed, Square, Clover, Ramp, Brex, Gusto, Stripe, etc.)
- 3–8+ years of full-cycle B2B SaaS sales experience with consistent top performance
- Proven success selling operational or financial products with AOVs between $10k–$100k+
- Strong financial fluency—comfortable discussing payments, cost structures, interchange, spend controls, or workflow automation
- You thrive in ambiguity, create your own structure, and enjoy building from zero
- Highly consultative, excellent at discovery, with strong demo and storytelling skills
- Comfortable carrying a quota where outcomes directly shape company trajectory
Experience That Stands Out
- Selling into industries with operational complexity (hospitality, retail, services, manufacturing, logistics)
- Exposure to products blending software + financial components (POS, payments, cards, lending, AR, AP automation)
- Experience selling to operators, controllers, CFOs, finance teams, and GMs
- Familiar with MEDDIC, SPICED, Sandler, or similar sales methodologies
- Proven success in both high-velocity and mid-market sales cycles
Why This Role Is Unique
- Founding AE: You set our sales culture, GTM motion, and revenue standards
- Massive Fintech TAM: Payments + spend automation + POS workflows are undergoing rapid modernization
- Direct Product Influence: Your deals shape product, UX, roadmap, and integrations
- High Upside: Competitive base, strong variable comp, and meaningful early equity
KPIs / How We Measure Success
- Achievement of monthly/quarterly new ARR targets
- Demo-to-close rate of 20–30%+ (depending on ICP)
- Healthy pipeline coverage (3–5× quota)
- Predictable and clean CRM hygiene
- Creation of repeatable playbooks and sales processes
- Strong partner/channel ecosystem development
- High customer satisfaction and clean handoff to onboarding