hero

Portfolio Careers

Build your career at the best companies in healthcare and fintech

Account Executive, Mid-Market (Expansion)

Blue J Legal

Blue J Legal

Sales & Business Development
Toronto, ON, Canada
Posted on Jan 17, 2026
Account Executive, Mid-Market (Expansion)
Toronto, Canada
Sales
Hybrid
Full-time

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 building an ambitious product roadmap and are looking for an Account Executive, Expansion to support growth across our portfolio of 4,000+ customers. As an Expansion Account Executive at Blue J, you will have the opportunity to own the end-to-end expansion sales cycle across a defined portfolio of existing customers. Reporting to the Director of Expansion, this individual contributor role focuses on driving revenue growth within our existing customer base through thoughtful account expansion, upsell, and renewals, while partnering closely with Customer Success and Sales to support strong, long-term customer outcomes.

A Note on Location

We are excited to meet with qualified candidates and are grateful for everyone’s interest. Please note that this is a hybrid position requiring candidates to be on-site in Toronto at least 3 days per week (4 days during the onboarding month).

The Opportunity

This is an opportunity to become an Expansion Account Executive at Blue J, the first role of its kind within the organization and an important part of how we grow revenue within our existing customer base.
As an Expansion AE, you will support a portfolio of existing customer accounts, with a clear focus on identifying, developing, and closing expansion opportunities across Blue J’s customer base. You will work across the full expansion lifecycle, from discovery through value realization, negotiation, and close, partnering directly with clients to build strong relationships, develop new use cases, and help customers realize the full value of our products.
This is a visible and impactful role that collaborates closely with teams across Sales, Customer Success, Marketing, and Product to deliver meaningful outcomes for our clients.

What You’ll be Doing

  • Identify, qualify and execute end-to-end expansion opportunities across your portfolio, driving upsell revenue from discovery through close.
  • Plan strategically within accounts, identifying high-potential expansion paths by analyzing usage patterns, customer outcomes, and emerging needs across teams.
  • Build trusted, consultative relationships with client stakeholders, ranging from champion to C-Suite decision makers, to understand customer business environments and position Blue J as a long-term strategic partner.
  • Partner closely with cross-functional teams including Customer Success, Product, Sales and Marketing to build compelling business cases and champion opportunities.
  • Lead expansion negotiations, navigating procurement cycles, objections and stakeholder alignment to close mutually valuable agreements
  • Help shape Blue J’s expansion motion, contributing to playbooks, messaging, and best practices as the team scales.

What You Offer Blue J

  • 5+ years of experience in a quota-carrying SaaS sales role, with demonstrated success driving expansion revenue within an existing customer base through upsell, cross-sell, and renewals, including ownership of meaningful ARR targets.
  • Proven ability to close expansion deals in complex, multi-stakeholder environments by building strong, trust-based relationships and selling consultatively to audiences ranging from day-to-day users to executive leaders.
  • Clear and effective communicator, able to translate technical or product concepts into compelling business value through written and verbal communication.
  • Comfortable operating in a data-informed way, using account insights, product usage, and customer signals to identify opportunities, prioritize efforts, and manage risk.
  • Highly organized and self-directed, with the ability to manage a full expansion sales cycle as an individual contributor, and motivated by ownership, collaboration, and the opportunity to help build and shape a growing expansion function.

What We Offer You

  • A high-impact role centered on growing and strengthening relationships with Blue J’s existing customers and supporting their long-term success.
  • The opportunity to contribute to and help evolve Blue J’s expansion sales approach as the business continues to scale.
  • A mission-driven culture focused on bringing clarity, efficiency, and accessibility to tax research for a diverse set of users and organizations.
  • A competitive compensation package that includes base salary, commission, stock options, and comprehensive benefits.
  • A flexible work environment that is primarily remote, with occasional opportunities to connect in person at our Toronto or Kitchener office and at industry events.
  • A collaborative and supportive team that values curiosity, respect, innovation, and learning, while making space for connection and fun.
  • The opportunity to grow with a fast-growing, well-funded company, supported by a strong product and a highly engaged customer community.

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 Dalia Vainer, Director of Expansion
Step 3: Meet with Sean Erjavec, CRO
Step 4: Present your ideas to Dalia 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.
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
Ready to apply?
Powered by
First name *
Last name *
Email *
LinkedIn URL *
Phone number *
Location *
Resume *
Click to upload or drag and drop here
Do you have any comments or accommodation needs you'd like to share?
Are you able to work on-site in our Toronto office 3 days per week as part of a hybrid schedule?
As you think about your next role, what compensation range would feel right for you?
By applying you agree to Gem's terms and privacy policy.
Save your info to apply to other roles faster & help employers reach you.
Req ID: R67