Vice President, Sales

About Blue J: Blue J is the leading generative AI solution for tax professionals. As a B2B SaaS company, our customers are accountants and tax experts who rely on our market‑leading software to deliver fast, accurate, and defensible answers to complex tax questions. Today, we support over 5,000 customers across the tax and accounting space.

Note on Location: This is a hybrid position requiring candidates to be based within commuting distance of Kitchener‑Waterloo or Toronto, with in‑office presence expected a couple of days each week. This role includes occasional travel for industry events, trade shows, and conferences. All candidates must be eligible to work in Canada.

Opportunity: This is an exciting opportunity for a strategic sales leader who thrives in a growth‑stage environment, with experience leading SMB and Mid‑Market sales organizations, owning both new logo acquisition and customer expansion revenue, and developing high‑performing teams. You’ll oversee an organization currently consisting of approximately 20 team members, with plans to scale the function to roughly 40 people over the short‑to‑mid term as the business continues its rapid growth trajectory. You’ll play a key role in shaping and executing our go‑to‑market strategy, building scalable sales motions, and fostering a high‑performing, customer‑centric culture.

What You’ll Be Doing

• Mentor and empower a team of 5 sales leaders responsible for both new business acquisition and customer expansion, fostering a high‑accountability, high‑performance culture centered around coaching, collaboration, and operational excellence.
• Grow the sales organization from ~20 to ~40 reps across new logo and expansion teams. Hire, onboard, and coach managers and individual contributors.
• Own strategy and execution for new logo acquisition and expansion motions.
• Own quota delivery for both new business and expansion; manage forecast, pipeline, win rates, ACV, and sales cycle.
• Work with sales enablement to implement scalable sales processes, playbooks, qualification framework, deal review cadence, and continuous training programs.
• Collaborate tightly with Marketing on demand generation and ABM, RevOps on forecasting & tooling, CS on handoffs and expansion plays, and Product on roadmap inputs.
• Partner with SalesOps to define KPIs, dashboards, territory design, compensation plans, and CRM best practices to ensure data‑driven decision making.
• Recruit high‑performing, diverse teams and foster a coaching culture with strong accountability and collaboration.
• Participate in strategic deals and executive relationships; ensure exceptional buyer and customer experience.

Success Metrics & Key Performance Indicators

• ARR growth (new logo ARR + expansion ARR)
• Quota attainment and percent of reps hitting quota
• Pipeline coverage and velocity
• Average contract value (ACV) and deal size growth
• Win rate and sales cycle length
• Customer retention/expansion rate and Net Revenue Retention (NRR)
• Ramp time for new hires
• Forecast accuracy

What You Offer Blue J

• 10+ years in B2B SaaS sales leadership with progressive management experience; proven track record scaling teams up to 50+.
• Experience at high‑growth startups (Series B–D) or hyper‑scale companies is highly valued.
• Familiarity with enterprise procurement and security/compliance requirements is an asset.
• Demonstrated success leading both new logo and expansion/renewal motions.
• Experience selling AI/ML, data, or adjacent sophisticated SaaS solutions (or to technical buyers).
• Strong cross‑functional collaboration with Marketing, CS, RevOps, Product and Partnerships.
• Hands‑on leader: comfortable in the field with strategic deals and building systems/processes.
• Data‑driven, operationally rigorous (CRM, forecasting, comp design, KPIs).
• Experience hiring and developing frontline managers.
• Excellent communication and executive presence; experience managing C‑level relationships.
• Comfortable in fast‑paced, ambiguous environments and building structure quickly.
• Comfortable leveraging AI tools and emerging technologies to drive efficiency, improve workflows, and stay ahead of industry trends.

What We Offer You

• Lead a pivotal stage of growth at a product‑driven AI SaaS company.
• Significant ownership over people, process, and revenue outcomes and the opportunity to build a best‑in‑class sales organization and influence company strategy.
• Flexible work arrangement: in‑office a couple of times a week at our downtown Toronto or Kitchener‑Waterloo offices to support team collaboration, with flexibility to work from home on remaining days.
• Competitive base salaries and stock options. Share in our long‑term success.
• Health‑friendly work/life balance with a comprehensive benefits package for you and your family.
• Supportive, collaborative culture that encourages growth and recognition.

The Core Values that Define Our Culture

• We are customer‑focused.
• We put the team’s interest before self‑interest.
• We are pleasant and playful.
• We are open to better ideas.
• We move fast and fix things.

Compensation: This is a Level 7 in Blue J’s career level framework. Final compensation will be set fairly based on experience, expertise, and alignment with role responsibilities, with the top of the range reserved for candidates who demonstrate exceptional depth, impact, and autonomy.

We believe our strength is built on diversity of thought. We value inclusiveness and are an equal‑opportunity employer. We do not discriminate based on race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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