Play a pivotal role as a Legal Director in a thriving SaaS environment. Collaborate cross-functionally, driving commercial contracting, corporate governance, and risk management as the organization scales. This position is designed for a strategic leader experienced in navigating complex legal matters. You'll partner closely with teams in Sales, Finance, and Product to guide legal support in rapid growth. Key responsibilities include managing negotiations, optimizing workflows, and advising on corporate initiatives, all while enhancing the legal tech infrastructure. Key Responsibilities: • Lead commercial contracting process from start to finish • Partner with Sales to streamline deal execution • Develop and implement contract lifecycle management systems • Support corporate governance and risk reporting • Advise on regulatory compliance initiatives Requirements: • 5+ years legal experience in commercial and corporate law • Strong legal foundation with an LL.B. or J.D. • Experience in a B2B SaaS environment preferred • Proficient in contract negotiation and drafting • Excellent communication and stakeholder management skills Shape and enhance the legal function while supporting business innovation in a growing tech landscape. #J-18808-Ljbffr
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 entering an exciting phase of scale and are looking for a Director, Legal to help support and guide the business through this growth. This role will play a key part in navigating complex legal matters, enabling the business to move quickly and thoughtfully, and partnering cross‑functionally to support product innovation, commercial strategy, and operational excellence. The Opportunity We’re hiring a Director, Legal to help build and scale our legal function during a period of rapid growth. In this role, you’ll partner closely with teams across Sales, Finance, People and Culture, Product, and GRC to lead commercial contracting and negotiations, support key corporate and regulatory initiatives, and manage external counsel as needed. You’ll play a hands‑on role in shaping how legal supports the business—driving efficiency through tools and automation, helping stand up a modern legal tech stack, and ensuring we can move quickly while managing risk effectively. A Note on Location This role is hybrid, with occasional in‑person time at our Toronto office as needed, along with attendance at company‑wide quarterly kickoffs. What You’ll Be Doing Lead commercial contracting end‑to‑end, including reviewing, drafting, and negotiating customer agreements (both on Blue J paper and third‑party paper) Partner closely with Sales and GTM teams to enable efficient deal execution while balancing risk and speed Build and optimize contract workflows, including helping to procure, implement and scale a contract lifecycle management (CLM) system Support corporate governance matters, including board and audit committee materials (e.g., risk reporting) Act as a legal partner to GRC initiatives, including privacy and regulatory compliance (e.g., GDPR), working cross‑functionally with internal stakeholders Provide legal support on strategic transactions, including financings, product‑related matters, and legal diligence processes Manage external counsel relationships, engaging firms selectively for specialized matters such as financings or complex transactions Advise on employment‑related matters as needed, in partnership with People & Culture Contribute to the development of Blue J’s legal function, including building scalable processes, implementing legal tech, and identifying opportunities for automation What You Offer Blue J 5+ years of relevant legal experience, ideally with a focus on commercial contracting and corporate matters A strong legal foundation, including a law degree (LL.B. or J.D.) Experience in a B2B SaaS environment is preferred, with familiarity navigating fast‑paced, high‑growth settings Proven ability to review, draft, and negotiate contracts with a practical, business‑oriented approach Strong judgment and ability to balance risk with business objectives Excellent communication and stakeholder management skills, with the ability to partner cross‑functionally Comfort operating in an evolving environment, with an interest in building processes and leveraging tools to scale the function What We Offer You A unique opportunity to shape and scale a modern legal function, leveraging systems, technology, and AI to drive efficiency and enable the business as it grows. 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 onsite meetings plus company kickoffs. 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 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 Chat with Deb, Director of Talent Acquisition Meet Grant, CFO Meet Avi, COO Connect with Ben, CEO Present your case study to the team 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. #J-18808-Ljbffr
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. #J-18808-Ljbffr
A leading generative AI company is seeking a Director, Legal to guide their legal function during rapid growth. This role involves leading commercial contracting, supporting corporate governance, and managing regulatory compliance initiatives. The ideal candidate will have over 5 years of legal experience, primarily in commercial matters within a B2B SaaS environment. This hybrid position offers flexibility with occasional in-person requirements at the Toronto office. Competitive salary and benefits are included. #J-18808-Ljbffr
OverviewJoin 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 LocationWe 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 OpportunityWe’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 DoingManage, 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 JYou 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 YouAn 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 CultureWe are customer-focusedWe put the team interest before self-interestWe are pleasant and playfulWe are open to better ideasWe solve the toughest problemsWhat to Expect in the Interview ProcessWe 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 ProcessStep 1: Chat with Deb, our Director of Talent AcquisitionStep 2: Meet Sean, our CROStep 3: In-depth follow-up with Sean, our CROStep 4: Presentation stage with Sean and other stakeholdersStep 5: Wrap up with Ben, our CEOWe 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. #J-18808-Ljbffr
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.
#J-18808-Ljbffr
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 entering an exciting phase of scale and are looking for a Director, Legal to help support and guide the business through this growth. This role will play a key part in navigating complex legal matters, enabling the business to move quickly and thoughtfully, and partnering cross‑functionally to support product innovation, commercial strategy, and operational excellence.
The Opportunity
We’re hiring a Director, Legal to help build and scale our legal function during a period of rapid growth. In this role, you’ll partner closely with teams across Sales, Finance, People and Culture, Product, and GRC to lead commercial contracting and negotiations, support key corporate and regulatory initiatives, and manage external counsel as needed. You’ll play a hands‑on role in shaping how legal supports the business—driving efficiency through tools and automation, helping stand up a modern legal tech stack, and ensuring we can move quickly while managing risk effectively.
A Note on Location
This role is hybrid, with occasional in‑person time at our Toronto office as needed, along with attendance at company‑wide quarterly kickoffs.
What You’ll Be Doing
Lead commercial contracting end‑to‑end, including reviewing, drafting, and negotiating customer agreements (both on Blue J paper and third‑party paper)
Partner closely with Sales and GTM teams to enable efficient deal execution while balancing risk and speed
Build and optimize contract workflows, including helping to procure, implement and scale a contract lifecycle management (CLM) system
Support corporate governance matters, including board and audit committee materials (e.g., risk reporting)
Act as a legal partner to GRC initiatives, including privacy and regulatory compliance (e.g., GDPR), working cross‑functionally with internal stakeholders
Provide legal support on strategic transactions, including financings, product‑related matters, and legal diligence processes
Manage external counsel relationships, engaging firms selectively for specialized matters such as financings or complex transactions
Advise on employment‑related matters as needed, in partnership with People & Culture
Contribute to the development of Blue J’s legal function, including building scalable processes, implementing legal tech, and identifying opportunities for automation
What You Offer Blue J
5+ years of relevant legal experience, ideally with a focus on commercial contracting and corporate matters
A strong legal foundation, including a law degree (LL.B. or J.D.)
Experience in a B2B SaaS environment is preferred, with familiarity navigating fast‑paced, high‑growth settings
Proven ability to review, draft, and negotiate contracts with a practical, business‑oriented approach
Strong judgment and ability to balance risk with business objectives
Excellent communication and stakeholder management skills, with the ability to partner cross‑functionally
Comfort operating in an evolving environment, with an interest in building processes and leveraging tools to scale the function
What We Offer You
A unique opportunity to shape and scale a modern legal function, leveraging systems, technology, and AI to drive efficiency and enable the business as it grows.
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 onsite meetings plus company kickoffs.
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 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
Chat with Deb, Director of Talent Acquisition
Meet Grant, CFO
Meet Avi, COO
Connect with Ben, CEO
Present your case study to the team
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.
#J-18808-Ljbffr
A leading generative AI company is seeking a Director, Legal to guide their legal function during rapid growth. This role involves leading commercial contracting, supporting corporate governance, and managing regulatory compliance initiatives. The ideal candidate will have over 5 years of legal experience, primarily in commercial matters within a B2B SaaS environment. This hybrid position offers flexibility with occasional in-person requirements at the Toronto office. Competitive salary and benefits are included. #J-18808-Ljbffr
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. #J-18808-Ljbffr
Play a pivotal role as a Legal Director in a thriving SaaS environment. Collaborate cross-functionally, driving commercial contracting, corporate governance, and risk management as the organization scales.
This position is designed for a strategic leader experienced in navigating complex legal matters. You'll partner closely with teams in Sales, Finance, and Product to guide legal support in rapid growth. Key responsibilities include managing negotiations, optimizing workflows, and advising on corporate initiatives, all while enhancing the legal tech infrastructure.
Key Responsibilities:
• Lead commercial contracting process from start to finish
• Partner with Sales to streamline deal execution
• Develop and implement contract lifecycle management systems
• Support corporate governance and risk reporting
• Advise on regulatory compliance initiatives
Requirements:
• 5+ years legal experience in commercial and corporate law
• Strong legal foundation with an LL.B. or J.D.
• Experience in a B2B SaaS environment preferred
• Proficient in contract negotiation and drafting
• Excellent communication and stakeholder management skills
Shape and enhance the legal function while supporting business innovation in a growing tech landscape.
#J-18808-Ljbffr
