Founding Enterprise Account Executive, North America

About This Role

This is a founding, high-ownership Enterprise Account Executive role where you’ll build October Health’s North America commercial motion from the ground up. You’ll be the face of October to US prospects for the first 12+ months—opening doors through your network, running complex HR tech evaluations, and closing personally. If you’re energized by creating something repeatable (not inheriting it), you’ll have unusual leverage to shape how October wins in the US. October helps companies build teams that adapt faster than change by continuously reading behavioural, operational, and engagement signals and turning them into clear patterns and recommended actions—then delivering performance psychology and behavioural change programmes directly to employees. In the US, your primary wedge will be October People (modern HRIS for 300–1,500 employee companies), with expansion into the broader October Health platform over time. Your impact will be measured in closed logos, ACV, and cycle predictability—and in the playbook you leave behind: messaging that lands with CHROs, a repeatable discovery and qualification framework, business-case templates, competitive displacement tactics, and a procurement/security path that removes friction. As the motion proves itself, you’ll either hire and lead the team around it or transition the motion to a VP of Sales—your path will be shaped by performance and your preferences.

Responsibilities

• Own the North America sales motion end-to-end: prospecting, discovery, demos, evaluation design, pricing, negotiation, and closing
• Build and maintain a high-quality outbound pipeline using your network and targeted account strategies for 300–1,500 employee US companies
• Lead rigorous discovery with CHRO/People/HR Ops stakeholders, tying October People to measurable outcomes (e.g., HR efficiency, data integrity, employee experience, retention, manager effectiveness)
• Create repeatable sales assets that future sellers can run: ICP definition, qualification criteria, messaging, business-case and ROI templates, mutual action plans, and competitive battlecards
• Navigate security, compliance, and procurement workflows (including HRIS integrations and identity requirements) and coordinate internal resources to remove friction and accelerate cycle time
• Run competitive displacement motions against incumbent HR platforms, multi-threading across HR, Finance, IT/Security, and Executive sponsors
• Partner tightly with Product and Customer teams to turn market feedback into roadmap inputs, packaging, and sharper positioning for the US mid-market

Requirements

Must-haves

• 8–12+ years of B2B SaaS sales experience, including 5+ years in HR technology (HRIS, payroll, performance, benefits, wellbeing, or an HR platform)
• Personally closed 15+ US mid-market/enterprise deals at $75K+ ACV in the last 24 months, with clear evidence of quota attainment and consistent pipeline generation
• Proven “founding US sales” experience: employee #1–5 in US sales at a B2B SaaS company that scaled from < $10M ARR to $30M+ ARR during your tenure, where you built (not inherited) the playbook
• A portable, active network of 40+ relationships with US Heads of People / VP HR / Head of HR Ops / CHROs at 300–2,500 employee companies, with recent (last 90 days) engagement
• Demonstrated ability to displace incumbents (e.g., Workday, ADP, BambooHR, Paychex, HiBob, Rippling) and run competitive, multi-threaded deal cycles through procurement, security, and legal
• Comfort operating as the only senior commercial person in-market: self-sourcing, building enablement artifacts, and collaborating directly with Product/Engineering/Clinical/Customer teams to win Nice-to-haves
• Direct experience in commercial/enterprise tiers at HiBob, Rippling, Lattice, Personio, 15Five, Deel, or a close peer
• Experience selling a foreign-HQ’d product into the US market and successfully handling the “not a US company” objection
• A documented sales artifact you personally created (redacted is fine) that is/was used in production: qualification framework, business case template, mutual action plan, competitive battlecards, or procurement playbook

Benefits

• Competitive compensation with a meaningful performance-based component (OTE aligned to senior, founding-scope impact)
• Fully remote role in North America with autonomy over your day-to-day and travel aligned to deal needs
• Direct access to experienced founders and a high-ownership environment where you can shape strategy, not just execute it
• Clear growth path as the US motion scales—opportunity to build and lead a team or step into a larger scope based on results and preference
• Mission-led work at the intersection of HR tech and mental health/performance, with a culture built on customer obsession, candor, learning, and teamwork