Director, Mid-Market Sales

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  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 IPA
500.
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…