Note: The job is a remote job and is open to candidates in USA. October is a company focused on helping organizations build adaptive teams through behavioral insights and performance psychology. They are seeking a Founding Enterprise Account Executive to establish and lead their North American commercial strategy, engaging with US prospects and driving sales for their HR technology solutions.
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
Skills
- 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
- 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
Company Overview