Head of Mid Market and SMB Sales

Toronto - Canada

Monthly Salary: Not Disclosed

Posted on: 25-10-2025

Vacancies: 1 Vacancy

Job Summary

At Deliverect our API-first platform is revolutionizing commerce by providing a connected suite of on and off-premise solutions. We empower both the food and retail industries to expand their revenue and simplify their operations creating seamless experiences for businesses to sell anywhere and deliver everywhere. Join us in this exciting journey where your contributions will directly impact how businesses connect with their customers in a rapidly evolving global market.

Your Impact

As the Head of Sales for SMB and Mid-Market North America you will take ownership of our growth strategy and execution across these critical high-volume segments. This is a crucial hands-on leadership role where you will define the regional sales strategy and directly accelerate customer acquisition and revenue growth across a massive market opportunity.

You wont just direct; youll be an active leader and coach leading by example in deal management and diving deep to optimize our operational processes. Your success will be measured by the performance and development of your team and your ability to seamlessly translate strategy into execution. By fostering a customer-centric sales culture and driving cross-functional alignment your leadership will be directly responsible for Deliverects continued scale and success in the restaurant space across Canada and the USA.

*This is a full-time hybrid role with a flexible work schedule offering 3 days in our Toronto office and 2 days of remote work.

What you will do

Lead and Develop High-Performing Teams: Provide exceptional people leadership to two Account Executive teams and one Team Lead fostering a culture of high performance accountability and respect. This involves hands-on coaching performance reviews individualized development plans and leading by example with a results-driven approach to consistently exceed sales targets.
Drive Full-Cycle Sales Strategy: Oversee and drive the entire full-cycle sales motion from initial lead generation and qualification (in partnership with Marketing & Partnerships) through negotiation and contract signature across the SMB and Mid-Market segments in NOAM. This includes setting ambitious regional sales goals defining effective outreach strategies and ensuring process efficiency to maximize conversion rates.
Optimize Operational Excellence: Dive into the details of existing sales processes. Proactively identify bottlenecks eliminate friction points and design/implement scalable efficient sales plays and workflows for our high-velocity segments.
Strategic Resource Management: Directly manage the regional sales budget and operational resources ensuring strategic allocation for technology training and personnel. You will be responsible for creating accurate and timely revenue forecasts leveraging CRM data to track performance and presenting insights and recommendations to senior leadership.
Champion Cross-Functional Alignment: Serve as the voice of the NOAM customer collaborating closely with Partnerships Account Management Product Marketing and Customer Success/Post-Sales teams to ensure sales efforts are aligned with product roadmaps go-to-market strategies and the overall customer experience.
Innovate Sales Strategies: Proactively develop and implement new and innovative sales plays and outreach strategies to penetrate new market segments and design scalable efficient sales processes for high-volume segments to improve team performance and customer/partner experiences.

What you will Bring

7 years of progressive sales leadership experience in a B2B SaaS environment with a proven track record of exceeding sales targets specifically within the SMB and Mid-Market segments.
Mandatory experience in either the Food Tech/Hospitality industry or in a complex multi-product SaaS environment.
The ability to articulate and sell sophisticated solutions.
Demonstrated success in managing full-cycle sales teams covering lead generation qualification negotiation and closure.
A highly effective leadership styleyou are known for inspiring results through coaching accountability and leading by example.
Extensive experience with pipeline generation forecasting and optimization for high-velocity sales cycles.
Proficiency in utilizing CRM tools (e.g. HubSpot) for tracking performance and managing team activities.
Proven ability to manage resources and budgets to drive optimal sales performance and efficiency.
Fluency in English is essential with exceptional written and verbal communication skills.

Join Our Innovative Journey:

At Deliverect were not just building a platform; were redefining how restaurants and retailers connect with their customers globally. Were looking for agile ambitious and resourceful team members who are excited to tackle complex challenges take calculated risks and contribute to innovative solutions that shape the future of commerce.

What Youll Gain by Joining Us:

Invest in Your Growth-We provide a dedicated learning budget to help you expand your skills and knowledge in this dynamic environment.

Solve Meaningful Challenges-Contribute to tackling some of the most significant challenges in the global tech industry directly impacting the way businesses operate worldwide.

Drive Innovation- Immerse yourself in a culture where innovation isnt just a buzzword our weekly releases and new features ensure youre always working on cutting-edge solutions.

Collaborate with a Global Team-Be part of a diverse international team that values transparency visibility and a multitude of perspectives.

Be Part of a Unicorn- Join a rapidly scaling SaaS unicorn at the forefront of the order management industry where your contributions have significant impact.

Enjoy Regionally Tailored Rewards- Our compensation and benefits packages are thoughtfully designed to reflect the unique needs of each market ensuring youre supported with what matters mostright where you are.

Our Commitment to Inclusion:

We are dedicated to building a diverse and inclusive workplace where everyone feels valued and has equal opportunities to succeed. We strongly encourage applications from underrepresented groups.

Important Information:

1. Fluency in English is required with strong written and verbal communication skills being essential.

2. Applicants must possess the legal right to work in the country where the role is based as we are currently unable to provide financial assistance for relocation or travel.

3. Please note that certain roles may require a background check as a condition of employment and you will be informed of this during the initial screening process.

If you require any accommodations or support during the recruitment process due to a disability please do not hesitate to contact us at emailprotected.

Ready to shape the future of commerce with us Explore our opportunities and apply today!

We may use artificial intelligence (AI) tools to support parts of the hiring process such as reviewing applications analyzing resumes or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed please contact us.

Required Experience:

Director