VP Sales, North America

Selective Search; United States; Remote; USD 250,000 - 450,000; Full time

Job summary

Selective Search is advising a global enterprise insurer to appoint a hands-on VP Sales for North America. The role leads Account Executives and BD teams, drives new logos and existing-customer expansion, and builds credible forecasts with executive involvement in key deals.

The right candidate is an experienced enterprise SaaS sales leader who can raise deal quality, improve conversion and coach teams toward disciplined, measurable revenue outcomes.

Qualifications

• An experienced enterprise SaaS sales leader who is equally comfortable leading the organisation and working directly in complex deals.
• A proven closer of high-value enterprise transactions involving executive alignment, negotiation, commercial structuring, contracting and signature.
• Strong in enterprise deal strategy, forecasting, coaching and performance accountability.
• Comfortable working through commercial, technical, delivery and contractual friction.
• A leader who surfaces risk early, creates clarity and aligns cross-functional teams around the commercial outcome.
• Experience selling mission-critical platforms into insurance or another complex regulated sector is highly desirable.

Responsibilities

• Own the North America new-logo and existing-customer expansion number.
• Lead Account Executives and business development teams against defined target accounts, growth objectives and pipeline expectations.
• Drive disciplined execution from target account through qualified opportunity, contract and revenue.
• Increase conversion from existing sales activity rather than relying solely on more volume.
• Set clear standards for qualification, stage progression, deal quality and close readiness.
• Build a forecast based on customer evidence and commitments, not seller optimism.
• Inspect strategic opportunities personally and intervene where leadership involvement will materially improve the probability or quality of close.
• Lead executive negotiations, pricing strategy, commercial structuring and contracting on critical deals.
• Identify weak or stalled opportunities early and make explicit decisions: advance, change strategy, resource differently or exit.
• Coordinate Solutions, Product, Delivery, Finance, Legal and executive leadership around priority pursuits.
• Ensure commitments are commercially sound, economically attractive and executable.

Job description

Location: North America

Sector: Enterprise Insurance Software / SaaS

Type: Permanent Executive Appointment

The opportunity

Selective Search is partnering with a global enterprise insurance software company to appoint a hands‑on VP Sales for North America.

The sales foundation is established: Account Executives own targeted accounts and create opportunities, supported by business development capacity. The VP Sales will be accountable for converting that activity into qualified pipeline, executable deals and contracted revenue.

This is a frontline sales leadership role for an experienced enterprise software leader who can raise deal quality, improve conversion and forecast predictability, and engage directly in the strategic pursuits where executive intervention can change the outcome.

The mandate

• Own the North America new-logo and existing-customer expansion number.
• Lead Account Executives and business development teams against defined target accounts, growth objectives and pipeline expectations.
• Drive disciplined execution from target account through qualified opportunity, contract and revenue.
• Increase conversion from existing sales activity rather than relying solely on more volume.
• Set clear standards for qualification, stage progression, deal quality and close readiness.
• Build a forecast based on customer evidence and commitments, not seller optimism.
• Inspect strategic opportunities personally and intervene where leadership involvement will materially improve the probability or quality of close.
• Lead executive negotiations, pricing strategy, commercial structuring and contracting on critical deals.
• Identify weak or stalled opportunities early and make explicit decisions: advance, change strategy, resource differently or exit.
• Coordinate Solutions, Product, Delivery, Finance, Legal and executive leadership around priority pursuits.
• Ensure commitments are commercially sound, economically attractive and executable.

Core leadership accountabilities

Convert pipeline into revenue

Every material opportunity must have a credible path to close, clear customer sponsorship, an identified decision process and actionable next steps.

Improve deal quality

Establish consistent expectations for an executable enterprise deal. Inspect customer need, economic value, decision‑maker access, solution fit, competitive position, commercial structure, contracting and close.

Harden forecast accountability

Create a forecast the business can operate against. Separate pipeline, upside and commit clearly; surface risk early; and challenge movement that is not backed by customer evidence.

Lead the deals that matter

This is not an administrative layer above the sales team. The VP will become directly involved in deal strategy, executive engagement, negotiation and close planning while keeping the accountable seller in ownership.

Raise team performance

Coach the judgement, discipline and behaviours behind successful enterprise selling. Translate activity into customer conversations, qualified opportunities and revenue without creating unnecessary bureaucracy.

What success looks like

• First 90 days: every material opportunity has a defensible stage, customer‑backed next action, owner, close plan and forecast position. Risk is visible early and the VP knows the critical deals personally.
• By six months: pipeline is more durable, fewer opportunities repeatedly shift right, qualification happens earlier and sellers show stronger ownership of progression and close.
• By 12 months: North America operates a disciplined, high‑accountability sales motion in which leadership can understand what will close, when, why, what could prevent it and what intervention is required.

The right person

• An experienced enterprise SaaS sales leader who is equally comfortable leading the organisation and working directly in complex deals.
• A proven closer of high‑value enterprise transactions involving executive alignment, negotiation, commercial structuring, contracting and signature.
• Strong in enterprise deal strategy, forecasting, coaching and performance accountability.
• Comfortable working through commercial, technical, delivery and contractual friction.
• A leader who surfaces risk early, creates clarity and aligns cross‑functional teams around the commercial outcome.
• Experience selling mission‑critical platforms into insurance or another complex regulated sector is highly desirable.

The simplest description of the role: own the number, improve conversion, harden the forecast and get into the deals that matter.