Vice President, Sales

Blue J Legal Inc.; Toronto; On-site; CAD 180,000 - 260,000; Full time

Benefits offered by this job

Stock options

Flexible in-office schedule

Competitive base salary

Great benefits package

Job summary

Blue J Legal Inc. is seeking a strategic VP, Sales to lead a growth-stage B2B SaaS organization. You will oversee an ~20-person team now, with plans to scale to ~40, driving both new logo acquisition and customer expansion.

You’ll shape go‑to‑market, build scalable selling motions, and partner with Marketing, RevOps, CS, and Product to deliver predictable ARR growth. The role requires 10+ years in SaaS sales leadership, a track record of cross‑functional collaboration, and comfort with

Qualifications

• 10+ years in B2B SaaS sales leadership with scaling experience.
• Experience building and leading teams to 40+ reps in growth stages.
• Proven ability to drive new logo and expansion revenue.
• Strong track record managing executive relationships.
• Familiarity with enterprise procurement and security requirements.
• Data-driven with CRM, forecasting and KPI discipline.

Responsibilities

• Mentor and empower a team of 5 sales leaders to drive performance.
• Grow the sales org from ~20 to ~40 reps for new logo and expansion.
• Own strategy and execution for new logo acquisition and expansions.
• Own quota delivery, forecast accuracy, and pipeline management.
• Implement scalable sales processes, playbooks, and training.
• Collaborate with Marketing, RevOps, CS, and Product on GTM.
• Hire, onboard and develop frontline managers and ICs.
• Lead executive relationships and strategic deals with customers.

Skills

SaaS sales leadership

Scale teams

New logo sales

Expansion sales

Executive relationships

Cross-functional collaboration

Job description

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.

With the launch of our flagship generative AI product, we’ve consistently exceeded our revenue targets quarter over quarter and continue to accelerate our growth. Our product roadmap is ambitious, customer-focused, and designed to deliver exceptional value at speed.

Backed by our $122M USD Series D funding, we’re racing ahead with an exciting product roadmap and are looking for Vice President, Sales to support our growth. Reporting directly to our CRO, this role will own both new logo and expansion motions while partnering closely with the broader GTM team to build repeatable processes, hire and develop talent, and deliver predictable ARR growth.

A Note on Location

We’re excited to meet with qualified candidates and are grateful for everyone's interest. Candidates who are within driving distance of our Kitchener-Waterloo or Toronto offices will be expected to work from the office a couple of days each week. The role also includes occasional travel for industry events, trade shows, and conferences. All candidates must be eligible to work in Canada or the US.

The 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

• Leadership development: 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.
• Build and scale: Grow the sales organization from ~20 to ~40 reps across new logo and expansion teams. Hire, onboard, and coach managers and individual contributors.
• GTM execution: Own strategy and execution for new logo acquisition and expansion motions.
• Revenue ownership: Own quota delivery for both new business and expansion; manage forecast, pipeline, win rates, ACV, and sales cycle.
• Process & enablement: Work with sales enablement to Implement scalable sales processes, playbooks, qualification framework, deal review cadence, and continuous training programs.
• Cross-functional leadership: Work tightly with Marketing on demand generation and ABM, RevOps on forecasting & tooling, CS on handoffs and expansion plays, and Product on roadmap inputs.
• Data & systems: Worth with SalesOps to define KPIs, dashboards, territory design, compensation plans, and CRM best practices to ensure data-driven decision making.
• Hiring & culture: Recruit high-performing, diverse teams and foster a coaching culture with strong accountability and collaboration.
• Customer focus: 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 in 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.
• You’re 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.
• We are flexible! You'll be 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 the remaining days.
• We’re well‑funded and offer competitive base salaries and stock options. You’ll play a crucial role in our growth, and it’s important to us that you share in our long‑term success.
• We care about you as a whole person. You’ll have a healthy work/life balance and colleagues who respect it. We’ve mindfully put together a great benefits package that covers you and your family.
• We’ve got an amazing team. We’re mission‑driven and motivated by success, but we’re friendly, we’re collaborative, and we care about each other.
• We’ve got all the start‑up perks you’d expect, and are intentionally building a culture where you can pickleball if you want, feel safe to be yourself at work, and watch your career grow because your team has invested in you.

The Core Values that Define Our Culture

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

What to Expect in the Interview Process

We anticipate a high volume of applicants for this role and are excited to grow our team. A human will review each application and get back to you as soon as possible. We appreciate your patience and look forward to connecting with you!

Interview Process

Step 1: Chat with Deb, our Director of Talent Acquisition

Step 2: Meet Sean, our CRO

Step 3: In-depth follow‑up with Sean, our CRO

Step 4: Connect with Tina, President

Step 5: Presentation stage with Sean and other stakeholders

Step 6: Wrap up with Ben, our CEO

We believe our strength is built on diversity of thought, and encourage candidates from all backgrounds and experiences to apply. 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.

How We Use AI in Our Hiring Process

To ensure transparency, we want candidates to know that Blue J uses AI-enabled tools within our applicant tracking system to help organize applications and highlight profiles that match the key requirements for each role.

AI does not make hiring decisions.

Every application is reviewed by a member of our Talent team, and all decisions throughout the process are made by humans.

We use these tools to support efficiency and consistency, not to replace human judgment and we’re committed to a fair, thoughtful, and equitable experience for every candidate.

Compensation

This is a Level 7 in Blue J’s career level framework. We use levels to define the expected scope, autonomy, impact, decision‑making, and experience for each role.

Final compensation will be set fairly and thoughtfully based on experience, expertise, and alignment with the role’s responsibilities. While all candidates are expected to bring directly relevant experience, the top of the range is typically reserved for individuals who demonstrate exceptional depth in the role’s core competencies, a strong track record of impact in similar environments, and the ability to operate with a high degree of autonomy from day one.