VP of Sales, North America

Location: Remote, United States
Employment Type: Full-Time
Travel: Regular customer, team, and partner travel, with occasional international travel

About Our Client

Our client is a fast-growing data privacy and security technology company helping regulated enterprises safely unlock the value of sensitive data for development, testing, analytics, and AI.

The platform automatically discovers and protects sensitive information while generating realistic, privacy-safe data that allows organizations to innovate without exposing personally identifiable information (PII).

With approximately $2.85M in ARR, multi-year enterprise and government customers, and a strategic AWS partnership, our client is entering its next phase of North American growth. The company operates at the intersection of data privacy, cloud infrastructure, security, and AI, with strong traction across financial services, insurance, government, and other highly regulated industries.

The Opportunity

Our client is seeking a VP of Sales, North America to build and lead its North American go-to-market engine.

This is a true player/coach role for a sales leader who wants to build rather than inherit. You will lead and develop an existing team of three Account Executives while continuing to personally build pipeline, work strategic opportunities, and close enterprise business.

The mandate is clear: create a repeatable outbound motion, establish strong pipeline and forecasting discipline, develop the sales team, and accelerate North American revenue growth.

This role reports directly to the CEO and offers significant autonomy and ownership.

What You'll Do

• Lead, coach, and develop an existing team of Account Executives while continuing to carry your own pipeline and close business.

• Build a scalable outbound sales engine, including prospecting strategies, sequences, messaging, playbooks, and pipeline processes.

• Personally own strategic, full-cycle enterprise opportunities from prospecting and discovery through technical evaluation, negotiation, and close.

• Sell $100K+ ARR solutions through complex, multi-stakeholder sales cycles that can range from approximately 3 to 14 months.

• Engage senior technical and executive stakeholders, including CIOs, CISOs, Enterprise Architects, privacy leaders, and data and cloud executives.

• Establish forecasting rigor, pipeline hygiene, activity expectations, and accountability across the sales organization.

• Partner closely with Solutions Architecture during technical evaluations and proof-of-concept processes.

• Develop and leverage strategic technology and channel partnerships across the cloud and data ecosystem.

• Work directly with executive leadership to shape North American GTM strategy, vertical expansion, hiring plans, and revenue goals.

• Recruit and grow the sales organization as North American revenue scales.

What We're Looking For

• 10+ years of enterprise sales experience, ideally within B2B technology, SaaS, data infrastructure, cybersecurity, AI, or adjacent markets.

• 4+ years of sales leadership experience with demonstrated success coaching and developing Account Executives.

• Experience in a startup or scale-up environment where you have helped build sales processes, teams, or GTM motions.

• A genuine player/coach mentality. You are comfortable leading a team while continuing to prospect, build pipeline, and personally close strategic business.

• Proven success selling complex, high-value enterprise solutions with multiple technical and executive stakeholders.

• Experience building outbound pipeline rather than relying solely on inbound demand.

• Strong executive presence and the ability to credibly engage CIO, CISO, Enterprise Architecture, security, data, and cloud stakeholders.

• Experience creating structure in an ambiguous, high-autonomy environment.

• Strong command of pipeline management, forecasting, CRM discipline, multi-threading, consultative discovery, and complex deal orchestration.

• Technical curiosity and the ability to understand how a solution fits within a customer's broader data, security, and cloud architecture.

• High energy, urgency, resilience, and a willingness to stay close to the work.

Bonus Points

• Experience selling within the AWS ecosystem or through strategic cloud partnerships.

• Background in data privacy, cybersecurity, AI, cloud infrastructure, synthetic data, or data platforms.

• Experience selling into highly regulated industries such as financial services, insurance, healthcare, or government.

• Previous experience as an early or founding sales leader who personally built a sales motion from the ground up.

• Experience working with technology ecosystems such as AWS, Databricks, Snowflake, Guidewire, or similar platforms.

Why This Opportunity

This is an opportunity to have a direct impact on the growth of an emerging technology company at a pivotal stage.

You'll have the chance to:

• Own North America: Take meaningful responsibility for revenue growth and market penetration across the region.

• Build the engine: Create the outbound motion, processes, team structure, and operating cadence rather than stepping into a mature sales organization.

• Lead from the front: Stay involved in strategic deals while coaching and developing the team around you.

• Sell into a growing category: Work at the intersection of data privacy, security, cloud infrastructure, and enterprise AI adoption.

• Shape the organization: Influence hiring, vertical strategy, partnerships, sales methodology, and future GTM expansion.

• Operate with autonomy: Work directly with executive leadership in a remote-first environment with significant ownership over outcomes.

Compensation & Benefits

Our client offers a competitive executive compensation package that includes:

• Competitive base salary plus performance-based OTE

• Commission on personally closed ARR

• Override on team-generated ARR

• Equity

• Healthcare benefits

• Flexible remote work environment

• Optional coworking membership

• Company-paid business travel, including potential international travel

Interview Process

The interview process is designed to move quickly and is expected to take approximately two weeks:

1. Introductory conversation with the CEO

2. Structured interview with the CEO

3. Leadership panel with additional members of the executive team

4. Final decision and offer

Our client is looking for a hands-on sales leader who is excited to build, sell, coach, and lead. If you have successfully helped an early-stage organization create a repeatable enterprise sales motion and still enjoy being directly involved in winning business, this is an opportunity to make a significant impact.