General Information:Job Title: Director of Sales (Technology Delivery)Location: Toronto, ON (Onsite/Hybrid) Job Type: Full-Time Reporting Line: Chief Revenue Officer (CRO) / Chief Strategy Officer (CSO) Salary Range:• Base: $160k-$180k CAD per year• OTE: Up to 50% of base, paid on hitting targetsRole Overview:The Director of Sales, Technology Delivery is responsible for originating and closing API integration, software engineering, and systems implementation engagements.
This role requires strong technical commercial fluency and the ability to sell engineering outcomes while maintaining alignment with architectural feasibility and delivery capacity.
Mandate:- Drive revenue across integration, API, and engineering engagements
- Own technical discovery and solution shaping with clients
- Ensure deals are technically feasible and margin-protective
- Build relationships with IT, product, and engineering stakeholders
Must Have:10-15+ years selling technical services or engineering solutions
Experience with:
o API integrations
o System architecture
o Platform connectivity
Background in:
o System integrators, engineering firms, or SaaS ecosystems
• Experience selling into:
o 3PLs
o Retailers
o Enterprise IT organizations
Key Responsibilities:Engineering & Integration Sales- Build pipeline across 3PLs, retailers, and enterprise clients
- Identify integration and engineering opportunities
- Develop relationships with technical buyers and stakeholders
- Sell API builds, custom integrations, feature development
Funnel Management- Lead technical discovery sessions with client IT teams
- Shape integration and engineering solutions with architects
- Ensure feasibility across APIs, systems, and data architecture
- Own pricing, proposal development, and negotiation
Cross-Functional Solutioning- Work with Architects during pre-sales
- Ensure clear technical scoping before contract execution
- Protect delivery margin through structured proposals
Account Expansion- Expand integration and engineering scope within accounts
- Identify cross-sell opportunities across consulting and implementation
- Maintain ongoing client relationships
- Hand off advisory or implementation opportunities where appropriate
What Success Looks Like in the First 90 Days:30 Days In- Build alignment with engineering and architecture teams
- Understand capacity constraints and margin thresholds
- Identify integration-focused pipeline targets
- Develop technical account maps
60 Days In- Generate qualified engineering pipeline
- Lead structured technical discovery sessions
- Submit technically validated proposals
- Close early integration or feature-build engagements
90 Days In- Demonstrate technology delivery bookings
- Improve pipeline coverage within lane
- Show disciplined margin-aligned deal structuring
- Deliver forward-looking technical revenue plan
Key Performance Indicators (KPIs):- Technology delivery bookings
- Average project margin
- Technical win rate
- Forecast discipline
- Expansion revenue within the lane
Perks you'll appreciate: Health & Wellness - Comprehensive health and dental coverage for you and your family (region-specific plans)
- Employee wellness programs where applicable
Time Off - Competitive paid time off (PTO), sick leave, and public holidays
- Flexible leave policies that respect local labor standards
Retirement & Financial Security - Retirement savings programs and employer contributions
- Region-specific plans (401(k) in the U.S., CPP and supplementary plans in Canada)
Professional Growth - Dedicated learning and development budget
- Support for skills development, leadership growth, and career progression
Flexible Work - Remote and hybrid work options
- Flexible working hours aligned to role and client needs
Additional Perks - Equipment and workstation allowances
- Internet and business travel reimbursements
- Employee stock options (ESOP), where applicable
- Team events, meetups, and company offsites
