Cross-industry, insurance-first | Global remit | Americas-based, remote | Reports to the Chief Commercial Officer
The role
This is not a standard VP of Sales job. Insurance is our core growth driver and this role goes deepest there, but it carries the whole company number across life sciences, public sector and OEM as well, worldwide. It also has to absorb sellers and systems from an acquisition, and leave the sales function in a state that stands up to institutional scrutiny.
You will inherit a small, capable team and an open field. We are blending a startup mentality with an established business, so you can innovate faster while deploying proven sales tactics and processes that work. You are building the machine: territory and quota design, capacity planning, methodology, deal inspection, and a forecast the Board can rely on. You report to the Chief Commercial Officer and sit on the commercial leadership team.
You will also sell. At our current team size this is a working leadership role, and you will personally lead the largest opportunities in your first two quarters.
The details
Role
Vice President of Sales
Reports to
Chief Commercial Officer
Scope
All new ARR worldwide, cross-industry, with an insurance-first focus
Team
Matrixed leadership with line-of-business General Managers (GMs) of the quota-carrying sales team, scaling with the plan
Location
Remote, based in the Americas. Global remit, with travel of approximately 30%.
Base salary
$175,000 to $200,000 USD
On-target earnings
$350,000 to $400,000 USD (50/50 base and variable, with accelerators above plan)
Equity
Participation in the management incentive plan, with change-of-control treatment
What you will own
- The number. Carry and deliver the company new ARR number worldwide, across all industries, direct and partner-influenced. You are based in the Americas and the remit is global, including EMEA.
- Team build. Recruit, ramp and coach the quota-carrying team. Expect to spend a meaningful share of your time on hiring. The team you build in your first six months is what shows up in bookings in your second year.
- Capacity and quota. Own territory design, quota assignment, and the sales capacity model. Quota is derived from rep productivity and carries deliberate over-assignment, not calculated backwards from the target.
- Forecast integrity. Own a weekly forecast with defined stage exit criteria and conversion rates derived from actual closed-deal history. Forecast means high confidence, not hope.
- Insurance leadership. Go deepest in insurance. Own the executive relationships at target carriers, MGAs, TPAs and brokers, and make sure our claims and underwriting story lands with operators, not just IT.
- Hold the differentiation line. Our biggest competitive risk is being boxed as another OCR or IDP tool by buyers who have been pitched by every extraction vendor and are now hearing agentic AI from their core platform vendor as well.
- Acquisition integration. Bring the acquired selling team onto one CRM, one pipeline, one forecast and one comp philosophy. Retain the sellers worth retaining, resolve account conflict, and deliver the cross-sell the acquisition was underwritten on.
- Cross-functional partnership. Partner with the Industry General Managers on vertical strategy and named accounts, with Marketing on pipeline coverage, with Strategic Partnerships on partner-sourced opportunities, and with Revenue Operations on quota, comp mechanics and reporting.
- Institutional readiness. Keep the sales function audit-ready. Cohort retention, quota attainment distribution, pipeline quality, win-loss, sales cycle by segment and forecast accuracy history should be current at all times, not reconstructed under deadline.
What you bring
- Scale experience. You have taken B2B software businesses from $2M to $50M or more in ARR in a sales leadership seat. You can speak precisely to ARR, seller count and per-rep productivity at the start and the end.
- Insurance depth. You have sold into insurance carriers, MGAs, TPAs, brokers or reinsurers and can hold a conversation with a Chief Claims Officer or Chief Underwriting Officer on their terms. You understand the claims and submission lifecycle, loss ratio and expense ratio, cycle time, leakage and straight-through processing. You know your way around Guidewire, Duck Creek and the wider core and content stack, and around ACORD and ISO forms, NAIC and state DOI expectations.
- Cross-industry range. You have carried a number across two or more unrelated verticals at the same time. You know how to keep a small team focused without letting one vertical starve the others.
- Global remit. You have led sellers or carried a number across more than one region, including Europe. You know how deal cycles, buying norms and employment practice differ outside North America, and you can run a team you do not sit beside.
- A team you built. You have personally recruited and ramped five to eight quota carriers. You can name them and say where they are now.
- Operating rigor. You build quota from steady-state rep productivity, plan for ramp, and can explain your capacity model on a whiteboard. You track attainment as a distribution, not an average.
- Acquisition integration. You have merged two selling teams after an acquisition. You have made the single versus dual go-to-market call, harmonized comp and territories without losing the people who mattered, and consolidated onto one pipeline.
- Exit experience. You have owned the sales side of a sale process or major diligence. You know what a buyer or banker asks the sales organization for, and what breaks when the data does not hold up.
- Enterprise and regulated selling. You are credible on AI without overselling it. You sell business outcomes and defensible data, not model hype.
- A working leader. You are still close enough to the work to run a deal yourself, and you want to be. You take coaching as readily as you give it.
- Bachelor's degree or equivalent practical experience.
Nice to have
- Experience in a private equity backed company with a defined growth mandate and reporting cadence.
- Relationships in the insurance systems integrator ecosystem, including Guidewire and Duck Creek implementation partners.
- Experience selling AI, intelligent document processing or data platform solutions into regulated industries.
- Life sciences or public sector selling experience alongside insurance.
- Experience selling in Canada and Latin America as well as the United States.
What is in it for you
This is a rare shape of role: enough scale that the fundamentals exist, enough whitespace that you will build most of what matters, and a clear horizon to build toward. You will have direct access to the CEO and the Board, and your work will be visible in every conversation about the company's value.
Adlib's headquarters are in Burlington, Ontario. This role is remote and based in the Americas, with a global remit. We care about employee health and wellness and build programs around personal and professional satisfaction. Our employee programs and benefits include, but are not limited to:
- Wellness and lifestyle spending account
- RRSP or 401(k) matching
- No limit vacation
- Extended maternity and paternity leave
- Employee assistance programs, and much more
To learn more about this role, please express your interest here, or follow us on LinkedIn for future opportunities.
