Founding Sales Leader
About The Position
We are looking for our first dedicated sales hire — a Founding Account Executive who wants to build something, not inherit something. This is the role where you help create the market, build pipeline, shape the narrative, and close the first repeatable deals. This is not a quota-and-commission role at a company where marketing hands you leads and a BDR team handles prospecting. This is the role where you show up, figure it out, and close deals that shape what this company becomes. This is also not a simple license sale. No two deployments are exactly the same. Every customer has different renewal motions, CRM structure, data quality, partner complexity, governance requirements, and business goals. You need to be comfortable selling the art of the possible while grounding the conversation in measurable revenue outcomes. You will sell a renewal enhancement platform for companies that already have systems/CRM, customer success tools, billing platforms, product analytics, support systems, partner portals, but still struggle to turn those systems into consistent renewal execution.
Requirements
- 6 – 10 years of professional B2B SaaS, revenue technology, CRM-adjacent, renewal, or complex technology-enabled sales experience.
- Track record of closing consultative, multi-stakeholder deals in the $50K–$250K ACV range (comfortable with $25K–$150K deal sizes, with proven experience closing $100K+ enterprise deals).
- Demonstrated ability to source and close pipeline independently from scratch without relying on BDRs or inbound marketing volume.
- Strong understanding of recurring-revenue metrics, including NRR, GRR, ARR, churn, downsell, expansion, renewal rate, and retention economics.
- Deep understanding of CRM systems, especially Salesforce, including how revenue teams utilize account, opportunity, renewal, activity, ownership, and forecast data.
- Ability to sell a highly conceptual, configurable solution where no two customer deployments are identical.
- Strong executive presence, outstanding written communication, and the ability to translate ambiguous operational pain into a clear, measurable business case.
Nice To Haves
- Direct experience selling Customer Success platforms, renewal management, revenue intelligence, CRM, subscription billing, workflow, data, or integration platforms.
- Previous experience working with companies or within ecosystems such as Gainsight, ChurnZero, Totango, Planhat, Salesforce, Clari, Gong, People.ai, Outreach, Salesloft, Zuora, Chargebee, Workato, MuleSoft, ServiceNow, or early-stage B2B SaaS startups.
- Proven experience selling directly to Chief Customer Officers, VP of Renewals, VP of Customer Success, CROs, RevOps leaders, CFOs, or Channel/Partner executives.
- Experience selling into organizations that utilize both direct and partner-led revenue motions.
- Prior experience at a Series A or Series B startup where the GTM motion was actively being built and refined.
Responsibilities
- Build and manage your own pipeline through outbound prospecting, network activation, event engagement, referrals, and targeted account development.
- Run end-to-end sales cycles from discovery and qualification through proposal, business case, negotiation, and close.
- Lead discovery conversations that uncover renewal pain, data fragmentation, CRM limitations, manual preparation, late engagement, coverage gaps, lifecycle selling constraints, and partner execution challenges.
- Educate buyers on the shift from workflow automation to work automation and the execution gap it closes, demonstrating how our platform enhances existing systems rather than forcing a rip-and-replace decision.
- Explain practical AI value in renewal operations, including signal interpretation, prioritization, guided action, content preparation, and human-governed execution.
- Leverage reference customers (including Red Hat) to open enterprise-level conversations.
- Work directly with the founding team to refine the ideal candidate profile (ICP), messaging, pricing, packaging, proof points, and go-to-market strategy.
- Translate customer and market feedback into sharper product, positioning, and GTM decisions.
Benefits
- A comprehensive benefits package (Health, Dental, Life Insurance and RRSP).
- Remote work. (available options).
- The opportunity for career growth and development.
- A collaborative and inclusive work environment.
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
