Head of Strategic Sales, North America

About the role

We are looking for successful candidates to be based on the East Coast. We are open to candidates in the US and in Canada. 

The Head of Strategic Sales, North America, will build and lead Adaptavist's regional Strategic Accounts programme, reporting to the Head of North America Sales and leading a team of Strategic Account Directors and Strategic Account Managers.

The role is accountable for creating a repeatable growth strategy across Adaptavist's highest-potential North American customers, maximising wallet share by connecting executive customer priorities to the full Adaptavist portfolio, the two selling motions - DevOps & Developer Experience and Service & Work Management - and the strategic partner ecosystem.

This is a hands-on sales leadership role requiring deep Strategic Account expertise, strong C-suite credibility and disciplined account governance. The successful leader will create high-quality account plans, accelerate complex opportunities, build multi-year, services-led relationships, and develop a team capable of consistently growing accounts with >£1m in annual gross-margin potential.

What you'll be doing

Strategic accounts programme build

• Define the operating model, coverage standards and governance for the North America Strategic Accounts programme in alignment with the Head of North America Sales and global sales strategy.
• Identify and prioritise accounts with the strongest potential to deliver sustained strategic value and >£1m annual gross-margin contribution.
• Establish consistent account-planning standards covering customer strategy, executive relationships, whitespace, partner alignment, competitive position, pipeline and multi-year growth objectives.
• Create a clear portfolio view of account health, potential, risk and required investment, ensuring the strongest talent is aligned to the highest-value opportunities.

Drive wallet share & account growth

• Build a growth strategy for each priority account that expands Adaptavist from point solutions and licence transactions into broader, services-led transformation relationships.
• Increase wallet share through multi-year consulting, managed services, optimisation and strategic partner solutions linked to measurable customer outcomes.
• Drive both DevOps & Developer Experience and Service & Work Management selling motions across the portfolio, identifying cross-sell opportunities and connecting customer priorities to repeatable propositions.
• Improve average order value, account penetration, renewal quality and the proportion of revenue/gross margin coming from strategic services.

Executive customer & deal leadership 

• Build and maintain C-level relationships across priority Strategic Accounts, acting as an executive sponsor and trusted advisor where appropriate.
• Coach the team to develop multi-threaded relationships across CIO, CTO, Engineering, Operations, Finance, Procurement and business stakeholders.
• Lead from the front on the most complex and material opportunities, helping shape value cases, executive engagement, commercial strategy and negotiation.
• Ensure account teams understand the customer's business agenda and can articulate Adaptavist value beyond individual technologies or products.

MEDDPICC, pipeline& forecast discipline

• Embed MEDDPICC as the common qualification and coaching framework across Strategic Accounts.
• Maintain sufficient qualified pipeline coverage to support strategic account growth objectives and to identify pipeline gaps early.
• Run a rigorous deal-inspection and forecast cadence focused on business metrics, economic-buyer access, decision criteria, decision process, paper process, identified pain, champions and competitive position.
• Improve win rates, deal velocity and forecast accuracy by coaching account leaders on evidence-based next actions and prioritisation.

Partner & global account alignment

• Develop strong relationships with regional partner leadership and partner account teams across Atlassian, GitLab, Harness, AWS, Datadog and other priority vendors.
• Create joint account plans and co-sell strategies that expand executive access, pipeline and services opportunities in target accounts.
• Coordinate North American account activity with global strategic-account programmes, ensuring a consistent customer strategy across regions.
• Leverage the partner ecosystem to strengthen differentiation and increase Adaptavist share of the customer transformation agenda.

Cross-functional strategic account execution

• Build integrated account teams across Sales, Presales, Delivery, Marketing, Finance, RevOps and Partnerships for priority customers.
• Ensure early alignment on customer outcomes, solution scope, delivery capacity, commercial assumptions and gross-margin expectations.
• Use Delivery insight, customer value realisation and managed-service relationships to identify and progress expansion opportunities.
• Create clear escalation paths and executive governance for the most material customer, commercial and delivery risks.

Leadership, coaching & talent development

• Lead, coach and develop a high-performing team of Strategic Account Directors and Strategic Account Managers.
• Set clear standards for account planning, opportunity creation, executive engagement, pipeline quality, forecast accuracy and customer ownership.
• Use regular one-to-ones, account reviews, deal reviews and skill coaching to improve individual performance and build repeatable excellence.
• Recruit and retain top strategic-sales talent, maintain an active bench, and address performance or capability gaps decisively.

Business management & operating rhythm

• Establish a repeatable cadence for portfolio reviews, account plan inspection, pipeline generation, opportunity coaching, and forecast governance.
• Use data to identify account growth trends, whitespace, performance gaps and resource priorities across the portfolio.
• Provide the Head of North America Sales with a clear view of strategic account performance, risks, investment needs, and expected growth.
• Share best practices across the wider North American sales organisation and help raise enterprise account-planning capability beyond the Strategic Account team

What we're looking for

• Proven leadership experience in Strategic Account sales within North American enterprise technology, consulting, SaaS, DevOps or adjacent ecosystems.
• Strong personal track record of winning and growing large, complex enterprise accounts and multi-year transformation engagements.
• Demonstrable experience building or operating a strategic/global account programme with structured account governance.
• Ability to maximise wallet share through account planning, whitespace identification, cross-sell and executive sponsorship.
• Deep understanding of services-led selling alongside software, licence or partner-led motions.
• Demonstrated use of MEDDPICC or an equivalent structured sales methodology for coaching, qualification and deal inspection.
• Strong C-suite credibility and the ability to lead complex customer, commercial and negotiation conversations.
• Experience developing joint account plans and co-sell motions with strategic technology partners.
• Proven ability to recruit, coach, develop and performance-manage senior account directors and managers.
• Strong commercial acumen across revenue, gross margin, pipeline, pricing, forecasting and account profitability.

A nice-to-have

• Experience in DevOps, Developer Experience, Platform Engineering, Cloud, Service Management or Work Management transformation, including work with strategic technology ecosystems such as Atlassian, GitLab, Harness, AWS or Datadog.