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Account Executive, Mid-Market

Blue J Legal

Blue J Legal

Sales & Business Development
Toronto, ON, Canada
CAD 30k-60k / year + Equity
Posted on Nov 27, 2025
Account Executive, Mid-Market
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 racing ahead with an exciting product roadmap and are looking for a Mid- Market Account Executive to support our growth. Reporting directly to our Director of Mid-Market Sales, this role will focus heavily on driving our growth, scale our efforts, and seize new opportunities in this exciting phase!

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 1-2 days per week (4 days during the onboarding month). The position also involves occasional travel across North America for events. All candidates must be eligible to work in Canada. (And travel to the US)


The Opportunity

We’re seeking a driven Account Executive to help accelerate our growth heading into 2026 and beyond. In this role, you’ll act as a trusted advisor to new customers, building strong relationships, uncovering their unique challenges, and demonstrating how our solutions deliver meaningful impact. Success will come from your ability to quickly master our product, understand our industry, and articulate our value with confidence.
You’ll take full ownership of the end-to-end sales cycle for mid-market accounting firms across North America, with opportunities to expand into additional U.S. markets as we scale. This role comes with quarterly and annual targets aligned to your territory. We’re looking for someone who thrives in a fast-paced, innovative environment and is motivated by contributing to a rapidly growing organization.

What You’ll be Doing

  • Ramp quickly by developing a strong understanding of Blue J’s product, customers, and sales process, approaching every interaction with curiosity and a growth mindset.
  • Run full-cycle, mid-market sales across the U.S. and Canada with a focus on hunting new logos within the IPA 500 (the largest U.S. accounting firms) and mid-sized Canadian firms.
  • Build and manage a balanced pipeline by self-generating opportunities and leveraging strong support from BDRs and Partnerships while using data to prioritize outreach and maintain momentum.
  • Lead consultative, multi-stakeholder sales cycles by guiding prospects through discovery, in-depth product demos, solution alignment, and pricing proposals with clarity and empathy.
  • Propose and negotiate pricing for deal sizes averaging approximately $40K while also managing complex opportunities that may reach $100K–$200K or more.
  • Partner closely with BDRs on high-quality handoffs, provide prospecting strategies when helpful, and contribute to a collaborative and team-oriented culture.
  • Share product feedback gathered from customer conversations to help inform future roadmap decisions and deepen our understanding of the market.
  • Maintain an active and authentic LinkedIn presence to support brand visibility, share insights, and engage with industry professionals.
  • Represent Blue J at industry events and trade shows, both virtually and in person, several times per quarter while building relationships and learning from the market.
  • Contribute to achieving quarterly and annual revenue targets, including approximately 2-5 new deals per month, through disciplined pipeline management, resilience, and strong execution.

What You Offer Blue J

  • 5+ years of mid-market sales experience as an Account Executive in software or a related industry, with proven success managing the full sales cycle and consistently closing high-velocity deals in the $30,000–$60,000 CAD range.
  • Skilled in influencing mid-market decision-makers and guiding C-suite, head of tax, or partners through evaluations, acting as a trusted advisor by conducting deep discovery and demonstrating clear value.
  • Strong business acumen, able to confidently discuss all but the most technical aspects of our products and articulate how Blue J creates meaningful outcomes for customers.
  • Customer-obsessed approach grounded in understanding who benefits most from our product, the value they gain, and how we stand out from alternatives.
  • Effective management of a full sales pipeline, including running in-depth product demos, proposing and negotiating pricing, and meeting or exceeding monthly and annual targets.
  • Collaborative and empathetic team member who works cross-functionally and supports BDRs through prospecting guidance, strategy sharing, and best practices.
  • Maintains a strong LinkedIn presence by promoting marketing content and building relationships across the industry, and represents Blue J at trade shows and conventions when needed.
  • Flexible and adaptable in a fast-growing environment, comfortable navigating change and evolving priorities with an open and growth-oriented mindset.
  • Highly accountable, willing to roll up your sleeves, dig into data, solve problems quickly, and deliver results with limited resources.

What We Offer You

  • A rare opportunity to be an early team member shaping the sales function at a rapidly growing company.
  • A high-leverage pipeline approach that pairs required outbound motion with a reliable, predictable stream of inbound opportunities from marketing and partnerships, fueling a clear path to exceed targets and consistently hit (or surpass) OTE.
  • We invest in your growth. Ongoing learning through regular coaching, training, and skill development, supported by a team that values continuous improvement.
  • We’re performance-driven, and it shows: Blue J has hit or exceeded its revenue goals for ten consecutive quarters, and every Mid-Market rep has surpassed their plan in both 2024 and 2025. You’ll be joining a high-performing team that’s winning and knows how to scale success.
  • We lead with trust, not micromanagement. Leadership is grounded in trust, autonomy, and empowerment, giving you the space to own your goals and the support to grow.
  • A culture built on meaningful connection, whether through in-person collaboration, team meetups, or company-wide events.
  • We’re well-funded and offer competitive base salaries, comprehensive benefits plans 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 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.

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 C., our Sr. Talent Acquisition Manager
  • Step 2: Meet Maegan Bjelajac, Director, Mid-Market Sales
  • Step 3: Meet Sean E., CRO
  • Step 4: Present your ideas to Maegan and Sean (CRO)
  • Step 5: Wrap up with Ben A., 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.
Req ID: R55