Dustin S.

Head of Sales | VP Sales | GTM Leader | Enterprise Sales | Revenue Systems Builder

Toronto, Ontario, Canada

About

I build and scale revenue engines. I operate at the intersection of enterprise sales execution and go-to-market system design — helping companies generate pipeline, close complex deals, and move from early traction to predictable, scalable revenue. My experience spans B2B SaaS, enterprise and mid-market sales, and revenue operations across cybersecurity, IoT, and infrastructure markets. I’ve led revenue functions across sales, partnerships, and GTM strategy, with a focus on building systems — not just hitting numbers. At AirMatrix, I built the company’s go-to-market function from the ground up — defining ICP, positioning, pricing, and enterprise sales motion while closing $1.2M+ in revenue and building an $80M+ pipeline across government, defense, and infrastructure sectors. At Zenduit, I rebuilt the revenue engine across sales and partnerships — implementing pipeline governance, forecasting discipline, outbound and partner-led pipeline generation, resulting in 227% attainment and $3M+ in TCV generated. Previously at DigiCert, I closed $1.8M+ in enterprise contracts (up to $500K+) across Fortune 500, healthcare, financial services, and public sector organizations, executing complex, multi-threaded sales cycles from prospecting through technical validation, procurement, and close. What differentiates my approach: • Pipeline generation (outbound prospecting, inbound demand generation, partner-sourced pipeline) • Revenue operating systems (forecasting, qualification frameworks, CRM governance, attribution models) • Enterprise deal execution (multi-threaded, technical and executive stakeholders) • Channel partnerships and partner ecosystem design (resellers, alliances, channel-led growth) • Scalable GTM processes that improve conversion, forecast accuracy, and revenue predictability I’m most effective in environments where growth isn’t fully solved — building the systems, teams, and strategy required to scale revenue.

Experience

  • Head of Sales & GTM | 2025 – Present at ZenduIT
    Jan 2025 - Present · 1 yr 6 mos

    IoT and fleet intelligence platform enabling real-time asset tracking, operational visibility, and infrastructure optimization. - Rebuilt full revenue engine across sales, partnerships, and demand generation - Designed and implemented pipeline governance, forecasting, and KPI systems - Built and scaled partner ecosystem (50+ resellers across NA, LATAM, EMEA) - Led enterprise deal execution across IoT and infrastructure solutions - Aligned outbound, inbound, and channel into unified GTM motion

  • Head of Sales / GTM | 2022 – 2024 at AirMatrix
    2022 - 2024 · 2 yrs

    AI-powered situational awareness platform integrating airspace, traffic, and public infrastructure data for government and enterprise operations. - Built and owned full GTM function across sales, partnerships, and marketing - Designed and executed GTM strategy (ICP, pricing, positioning, enterprise motion) - Repositioned company into AI-powered command & control platform - Built revenue operating system (CRM, forecasting, pipeline governance) - Built and managed $80M+ enterprise pipeline across government and infrastructure sectors

  • Enterprise Account Executive at DigiCert
    2020 - 2022 · 2 yrs

    Global cybersecurity and digital trust company providing PKI, certificate lifecycle management, and enterprise security infrastructure solutions. - Owned full-cycle enterprise sales across cybersecurity and PKI infrastructure - Closed complex multi-threaded deals across Fortune 500, healthcare, financial services, and public sector organizations - Managed the full deal lifecycle including prospecting, discovery, technical validation, procurement, legal negotiation, and contract execution - Worked across security, IT, procurement, and executive stakeholder groups to drive consensus and close - Drove net-new, expansion, and renewal revenue in a high-performance enterprise sales environment Results - $1.8M+ enterprise revenue closed - Multi-year deals up to $500K+ - Selected accounts included Veritas, WSIB, Texas Capital Bank, Franklin Templeton, Imprivata, FedEx, Adobe, Cloudera, Boston Scientific, Cummins, Honeywell, Johnson Controls, United Healthcare, Cisco Meraki, DXC, PBS, and GTAA

  • Director of Sales at Chartered Professional Accountants of Canada (CPA Canada)
    2017 - Feb 2020 · 3 yrs 2 mos

    National accounting organization serving over 250,000 members across Canada through education, partnerships, certification, and enterprise-level professional services. - Led national enterprise sales strategy across direct and distributor channels - Managed manager-level team structure across regional markets - Implemented segmentation, playbooks, KPI systems, and sales process standardization across distributed teams - Expanded channel contribution and improved execution consistency across the organization Results - 30%+ revenue growth - 25%+ increase in channel contribution

  • VP Sales & Business Development at goFleet
    2014 - 2017 · 3 yrs

    Fleet management and telematics company delivering vehicle, asset, and mobility solutions across North America through direct and channel sales. - Led revenue growth, GTM strategy, and sales execution across North America - Built and led a distributed revenue organization across direct sales and partner channels - Designed pricing, packaging, and recurring revenue strategy to improve monetization and lifetime value - Built and scaled a partner ecosystem as a core part of the GTM model - Owned forecasting, pipeline generation, and team performance systems Results - Scaled personal production from ~$500K to $1M+ ACV - Increased recurring attach rate from ~50% to ~70% - Drove 25–40% of total revenue via partners - Enabled 5000%+ U.S. expansion