Vice President, Sales Development

Blue J Legal Inc.; Toronto; On-site; CAD 180,000 - 240,000; Full time

Benefits offered by this job

Stock options

Competitive compensation and benefits

Hybrid work in Toronto

Job summary

Blue J Legal Inc. is seeking a Vice President of Sales Development to lead and scale a high-growth SDR/BDR organization.

You will own strategy, execution, and performance across outbound, inbound, and PLG motions, reporting to the CRO, with a focus on building a scalable pipeline engine. You will oversee a team of professionals, partner with Marketing, RevOps, and Product to optimize targeting, messaging, and conversion, and drive leadership development while expanding the team over the next

Qualifications

• 10+ years in SaaS sales leadership.
• 5+ years leading multi-layer SDR/BDR orgs.
• Proven success scaling SDR programs in high-growth SaaS.
• Experience supporting enterprise and mid-market sales.
• Strong outbound, demand gen, inbound, PLG understanding.
• Data-driven with scalable pipeline systems.

Responsibilities

• Develop and execute Sales Development strategy aligned with growth.
• Build org structure, cadence, accountability for rapid growth.
• Lead outbound, inbound, and PLG pipeline strategies.
• Establish KPIs, forecasting and reporting with RevOps.
• Collaborate with Marketing, Product, and CS for pipeline flow.

Skills

SaaS Sales

Team Leadership

Forecasting

Analytics

Executive Communication

Tools

CRM Systems

Job description

About Blue J

Blue J is the leading generative AI solution for tax professionals and one of Canada's fastest-growing AI companies. Headquartered in Toronto, we're a high-growth B2B SaaS company building industry-leading tax research software that helps accountants find accurate answers to complex tax questions with greater speed and confidence.

Backed by a $122M USD Series D funding round, we're scaling rapidly across North America and the UK while continuing to push the boundaries of what's possible with AI. By combining advanced technology with deep tax expertise, we empower tax professionals to work more efficiently, make better decisions, and deliver greater value to their clients.

A Note on Location

This is a hybrid role requiring candidates to work from our Toronto office 2–3 days per week, with occasional travel across North America. Candidates must be eligible to work in Canada.

The Opportunity

As Blue J enters its next growth phase, we're investing heavily in pipeline generation and sales development. We're looking for a Vice President, Sales Development to lead and scale our Sales Development organization. Reporting to our Chief Revenue Officer, you'll oversee a team of approximately seven Business Development and Inside Sales professionals, with plans to roughly double the organization over the next 12–18 months.

You'll own the strategy, execution, and performance of Sales Development, unifying outbound prospecting, inbound demand, and product-led growth (PLG) into a scalable pipeline generation engine. You'll establish the operating model, coaching framework, and technology strategy that enables the team to scale while leveraging AI to improve productivity, engagement, and performance.

This is a unique opportunity to build a world-class Sales Development organization at a pivotal stage of company growth. We're looking for a proven B2B SaaS leader who has successfully built and scaled Sales Development organizations, developed exceptional leaders, and created predictable, repeatable pipeline generation at scale.

What You’ll be Doing

Strategic Leadership

• Develop and execute Sales Development strategy aligned with Blue J’s growth objectives.
• Build the organizational structure, cadence, and accountability framework to support rapid growth.
• Set pipeline targets and performance metrics across outbound, inbound, and PLG motions.
• Serve on the Revenue Leadership Team, contributing to GTM planning, forecasting, and revenue strategy.
• Continuously improve methodologies, technology adoption, and productivity.

Team Leadership & Development

• Lead, coach, and develop Sales Development Managers and their teams.
• Build a high-performance culture of accountability, collaboration, and results.
• Recruit, retain, and develop top talent.
• Create leadership development programs, succession plans, and career paths.
• Establish best practices for management and coaching.

Pipeline Generation

• Lead outbound prospecting, inbound lead management, and PLG conversion strategies.
• Optimize segmentation, territory planning, qualification, and prospecting strategies.
• Drive adoption of modern outbound methods: multi-channel engagement, account-based selling, AI tools, automation.
• Partner with Marketing, RevOps, and Product to improve targeting, messaging, and conversion.
• Build scalable motions that convert prospects and product users into pipeline and revenue.

Operational Excellence

• Establish and monitor KPIs across meetings, pipeline, opportunities, and conversion.
• Improve forecasting accuracy.
• Partner with RevOps to optimize reporting, workflows, and technology.
• Analyze funnel performance and drive data-driven improvements.
• Evaluate AI/automation opportunities to boost efficiency.

Cross-Functional Partnership

• Partner with Sales to ensure consistent pipeline delivery and smooth handoffs.
• Collaborate with Marketing on demand generation and messaging.
• Work with Product/PLG leaders to maximize PQL conversion.
• Partner with Customer Success on expansion and cross-sell opportunities.

Key Performance Indicators

Success in this role will be measured by:

• Pipeline generated by Sales Development
• Qualified meetings booked and accepted
• Pipeline contribution toward revenue targets
• Outbound prospecting conversion rates
• PLG and inbound lead conversion rates
• Speed-to-lead performance
• Sales Development productivity metrics
• Forecast accuracy
• Manager and team retention
• Internal promotions and leadership development

What You Offer Blue J

• 10+ years in SaaS Sales, Sales Development, or Revenue leadership.
• 5+ years leading multi-layer Sales Development orgs through managers.
• Proven success scaling SDR/BDR orgs in high-growth SaaS while hitting pipeline targets.
• Experience supporting enterprise and mid-market sales.
• Deep understanding of outbound prospecting, demand gen, inbound pipeline, and PLG.
• Track record building repeatable pipeline systems and scalable models.
• Experience coaching frontline leaders and managers.
• Strong analytical, operational, and strategic capabilities with a data-driven approach.
• Excellent communication, executive presence, and stakeholder influence.
• Comfortable leveraging AI and emerging tech to improve productivity and workflows.

Nice to Have

• Experience in AI, automation, data, or enterprise software.
• Scaling SaaS orgs through ~$20M–$200M+ ARR.
• Familiarity with modern sales engagement, CRM, and revenue tech platforms.
• Experience supporting North American GTM orgs.

What Success Looks Like in Your First 12 Months

• Build strong alignment across outbound Sales Development, inbound demand, and product-led growth motions.
• Increase the efficiency, predictability, and quality of pipeline generation while consistently achieving pipeline targets.
• Improve conversion rates across outbound prospecting, inbound lead management, and PLG funnels.
• Develop a strong bench of Sales Development leaders through coaching, mentorship, and succession planning.
• Establish scalable operating processes, performance metrics, and management rhythms that support continued organizational growth.
• Become a trusted member of the Revenue Leadership Team and a key driver of Blue J's revenue growth.

What We Offer You

• A rare opportunity to build and scale a critical GTM function during one of the most exciting stages of Blue J's growth.
• A mission-driven culture where your work directly advances clarity, efficiency, and accessibility in tax research.
• Competitive base salary, stock options, and benefits designed to support you and your family.
• A collaborative, ambitious, and supportive team that values innovation, respect, and fun.
• The excitement of a fast-growing, well-funded company with clear momentum, and the resources to back bold initiatives.

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

• Chat with Natalie, Sr. TA Manager
• Meet Sean E, CRO
• 45-minute leadership deep dive with Sean
• Meet Tina, President of Blue J
• Present your case study
• Meet 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.

We strive to create an inclusive and accessible hiring experience for all candidates. If you need any accommodations during the interview process, please let us know in your application. Our team is dedicated to providing the necessary support and making reasonable adjustments to ensure a smooth process for everyone.

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.