Head of Mid Market and SMB Sales
Deliverect
Sales & Business Development
Toronto, ON, Canada
Posted on Oct 24, 2025
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 won't just direct; you'll 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 Deliverect's 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 style—you 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, we're not just building a platform; we're redefining how restaurants and retailers connect with their customers globally. We're 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 You'll 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 isn't just a buzzword – our weekly releases and new features ensure you're 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 you’re supported with what matters most—right 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 talent@deliverect.com.
Ready to shape the future of commerce with us? Explore our opportunities and apply today!