Director, Mid-Market Sales

Blue J; Toronto; On-site; CAD 120,000 - 160,000; Full time

Benefits offered by this job

Competitive base salary

Stock options

Flexible work environment

Great benefits package

Start-up culture perks

Job summary

A leading generative AI company in Toronto is seeking a Director of Mid-Market Sales to drive revenue and scale operations. The ideal candidate will have 7+ years of sales experience with a focus on mid-market strategies and team management. This hybrid role offers flexibility and the opportunity to contribute significantly to the company's growth trajectory. Passion for AI and a results-driven mindset are essential.

Qualifications

• 7+ years of experience in sales, with at least 5 years in a leadership role.
• Proven success managing mid-market sales teams.
• Experience with both inbound and outbound sales strategies.

Responsibilities

• Manage, mentor, and develop a team of Mid-Market Account Executives.
• Develop and execute inbound and outbound sales strategies.
• Drive overall team performance and meet or exceed revenue targets.

Skills

Sales leadership

Mid-market sales strategy

Coaching and mentorship

Consultative selling

Relationship building

Job description

Overview

Join to apply for the Director, Mid-Market Sales role at Blue J.

Blue J is the leading solution in generative AI for tax experts. We’re a B2B SaaS company whose customers are accountants, and our AI-tax research software is the best in the market. 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. We recently announced our $122M USD Series D raise, to accelerate innovation and deliver even greater value to tax professionals. We’re now looking for a Director, Mid-Market Sales to help us scale, drive revenue, and seize the massive opportunity ahead as we continue expanding across North America and into international markets.

A Note on Location

We are excited to meet with qualified candidates and are grateful for everyone’s interest, however this is a hybrid position requiring candidates to be based within commuting distance of Kitchener–Waterloo or Toronto, with in-office presence expected a couple days each week. This role includes occasional travel for industry events, trade shows, and conferences. All candidates must be eligible to work in Canada.

The Opportunity

We’re looking for a strategic, results-driven Director of Mid-Market Sales to join our growing team, reporting directly to our Chief Revenue Officer, Sean Erjavec. This is an exciting opportunity for a strategic sales leader who thrives in a growth-stage environment, with experience overseeing mid-market sales cycles, owning team targets, and developing high-performing teams through hands-on coaching and mentorship. In this role, you and your team will be targeting the 500 largest accounting firms in the US, namely IPA500.

In this role, you’ll lead and inspire a team of 3–6 Mid-Market Account Executives focused on consultative selling and strategic account development. You\'ll play a pivotal role in shaping our go-to-market strategy, leading and empowering your team to achieve their targets, while guiding them through multi-stakeholder sales cycles and strengthening executive-level engagement across accounts.

The ideal candidate has a proven track record of exceeding targets in the mid-market segment, a passion for developing sales talent, and a strategic mindset for scaling repeatable growth. You’ll help cultivate a culture of accountability, collaboration, and customer-centricity while refining processes and driving operational excellence.

Our ideal candidate is inspired by our mission and motivated to thrive in a fast-paced, innovative, and rapidly growing company. You’ll be instrumental in building a results-oriented, collaborative team culture while also developing strategies to drive business growth and ensure customer success.

What You’ll be Doing

• Manage, mentor, and develop a team of Mid-Market Account Executives, currently an initial team of 3 with plans to grow further. The team is responsible for both new logo acquisition and expanding existing customer accounts.
• Develop and execute inbound and outbound sales strategies to maximize pipeline generation, conversion rates, and overall revenue growth.
• Drive overall team performance and owning the collective quota, ensuring your team consistently meets or exceeds revenue targets through strategic coaching and execution.
• Monitor individual and team KPIs, providing coaching and feedback to ensure targets are consistently met or exceeded.
• Oversee accurate reporting of leads, pipeline, and forecasts on a regular basis.
• Develop and implement training and coaching plans to ensure your team is equipped with the skills, tools, and confidence needed to succeed.
• Work closely with marketing, product, and customer success teams to align sales efforts with broader company objectives and ensure a cohesive customer journey.
• Continuously refine sales processes, tools, and methodologies to enhance efficiency and effectiveness.
• Stay informed on industry trends and customer needs to drive strategic decision-making and maintain a competitive edge.

What You Offer Blue J

• You bring 7+ years of experience in sales, including at least 5 years in a leadership role, with proven success managing mid-market sales teams.
• You have a strong track record of thriving in fast-paced sales environments and consistently meeting or exceeding revenue targets.
• You’re experienced with both inbound and outbound sales strategies, from lead generation to pipeline management and closing deals.
• You excel at creating and implementing training and coaching programs that empower your team to grow and succeed.
• You know how to foster a collaborative, results-driven culture, inspiring your team to deliver their best work.
• You’re great at building relationships across teams and with customers, and you bring exceptional communication and interpersonal skills to the table.
• You know how to use metrics to optimize performance, and drive results.
• You’re not afraid to roll up your sleeves, contribute directly to sales efforts, and find practical solutions to challenges.

What We Offer You

• An incredibly exciting and rare opportunity to be an early employee building out the mid-market sales function at a rapidly growing company. We’re building a revolutionary tool from the ground up, and you will have a meaningful role in shaping the team that builds it.
• 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 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!

All candidates must be eligible to work in Canada, and live within reasonable commuting distance of our Toronto and/or Kitchener-Waterloo offices for in person meetings.

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: Presentation stage with 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.