Director, Expansion 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.

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.

On the heels of our $122M USD Series D funding, we’re racing ahead with an exciting product roadmap and are looking for a Director, Expansion Sales to support our growth. Reporting directly to our CRO, this role will focus heavily on driving revenue growth within our existing customer base through strategic account expansion and building the foundation for a scalable team.

A Note on Location

This role is primarily hybrid, with the expectation of occasional in-person meetings at our Toronto or Kitchener office and some travel for conferences.

The Opportunity

This is a unique opportunity to lead the continued growth of our customer base by developing and executing expansion sales strategies. As the first hire on Blue J’s expansion sales team, you’ll lay the foundation for future growth while shaping how the team evolves. The Director, Expansion Sales will act as a hands-on leader, engaging with clients to identify new opportunities within existing accounts. This role is key to shaping how Blue J deepens relationships with current customers and maximizes the value they receive from our products.

What You’ll be Doing

• Develop and implement targeted expansion strategies for Blue J’s 3,500+ clients across SMB, mid-market, and enterprise segments.
• Identify and pursue upsell and cross-sell opportunities to maximize account value.
• Build and maintain strong relationships with senior client stakeholders to understand their evolving needs.
• Collaborate with sales, customer success, and product teams to ensure alignment and customer satisfaction.
• Manage and prioritize a pipeline of expansion opportunities from qualification to close.
• Analyze performance metrics and adjust strategies to drive continuous improvement.
• Negotiate and close renewal and expansion deals that support company objectives.
• Maintain a deep understanding of customer accounts and industry trends to anticipate future opportunities.
• Over time, hire, develop, and lead a team to scale expansion sales across the customer base.

What You Offer Blue J

• 8+ years of sales experience in SaaS or technology sectors, with a strong focus on account expansion and upselling.
• Proven success in both executing and leading revenue growth initiatives.
• Strong leadership and coaching abilities, with interest in building a new function from the ground up.
• Excellent communication, relationship management, and negotiation skills.
• A proactive, hands-on approach and the ability to thrive in a dynamic, growth-focused environment.

What We Offer You

• A rare opportunity to shape and lead the growth of a high-impact expansion sales team that will play a key role in Blue J’s continued success.
• 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.
• Flexibility in how you work: primarily remote, with occasional travel to our Toronto/Kitchener office and conferences as needed.
• 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 deliver on our promises
• We solve the toughest problems

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 Natalie, our Sr. Talent Acquisition Manager

Step 2: Meet with Sean Erjavec, CRO

Step 3: Meet with Mat Armstrong, VP, Customer Success

Step 4: Present your ideas to Sean and other stakeholders

Step 5: 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.

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.