GTM Engineer - DockMaster

GTM Engineer - GTM Engineer - DockMaster About Dockmaster.com Dockmaster.com is the leading marina management platform serving entertainment attractions and venues across the waterfront industry. Our software powers dock operations, reservations, billing, and guest experiences for marinas nationwide. We’re building a modern revenue engine to match our ambitions — and this role is at the center of that transformation. The GTM Engineer is a hybrid builder–operator who designs and maintains the technical infrastructure that powers Dockmaster’s revenue engine. Rather than manually running sales and marketing operations, you’ll build systems that automate, scale, and optimize them. You’ll sit at the intersection of engineering, data, and go-to-market strategy — turning workflows that take hours into systems that run in seconds. In short: you don’t just run the playbook — you build the machine that runs it. Working cross-functionally with Sales, Marketing, Product, and Professional Services. You’ll be embedded within the revenue team but operate with significant autonomy — think of yourself as the engineering arm of the go-to-market organization. Collaborates With Sales (SDRs, AEs), Marketing, Product, Data, Professional Services, Product Manager, Sales, Marketing Lead. Why Dockmaster Ground-floor opportunity to build the entire GTM technical infrastructure from scratch Direct impact on revenue — your systems will power every dollar of new business Work alongside a leadership team that values speed, experimentation, and automation-first thinking Category-defining SaaS platform in a vertical with massive, untapped potential Autonomy to choose your tools, design your systems, and own the outcomes The successful candidate will be based anywhere in Canada, working in a remote work model! What your day will look like: Sales Automation and Productivity Build and maintain tools that dramatically increase SDR and AE productivity across the full sales cycle Design automated lead enrichment pipelines that append firmographic, technographic, and intent data to inbound and outbound leads in real time Build prospecting automation workflows that surface high-fit accounts based on ICP criteria and buying signals Architect CRM workflow automations in HubSpot to enforce pipeline hygiene, automate stage progression, and trigger internal notifications Develop AI-driven outbound messaging sequences that personalize at scale using prospect-specific context Create meeting booking automation to reduce scheduling friction and increase connect rates Growth, Infrastructure and Pipeline Generation Create the systems that generate and nurture a pipeline without constant manual intervention Build automated outbound campaign engines that execute multi-channel sequences (email, LinkedIn, phone) on a defined cadence Develop AI-generated personalized outreach at scale, adapting messaging to prospective industry, role, and stage Implement data scraping and lead sourcing workflows to build targeted prospect lists from public data sources Create trigger-based prospecting systems (e.g., a marina raises funding or announces expansion → AI detects → personalized outreach generated → SDR notified) Support product-led growth workflows that convert trial users into qualified pipeline AI-Powered GTM Leverage AI across the revenue stack to give Dockmaster an outsized competitive advantage in speed and personalization Build and manage AI SDR assistants that handle initial prospect engagement, qualification, and handoff Develop AI-generated demo environments and personalized demo prep packets Create AI proposal and SOW generation tools that reduce deal cycle time Implement AI call summary and coaching workflows that feed insights back into the sales process Build AI-based prospective research tools that deliver actionable account briefs before every call Data and Revenue Analytics Build the dashboards and models that give leadership real-time visibility into revenue performance Design pipeline analytics dashboards that track stage velocity, conversion rates, and bottlenecks Build and refine lead scoring models that prioritize the highest-value opportunities for sales Implement end-to-end conversion tracking across marketing and sales touchpoints Create experimentation analysis frameworks to measure the impact of GTM tests Develop attribution systems that connect marketing spending to closed revenue Experimentation and Rapid Growth Testing Run a high-velocity experimentation program that continuously improves GTM performance Target: 10–20 experiments per month Test different ICP segments to identify under-penetrated verticals within the marina and entertainment industry A/B test outreach messaging across channels, personas, and value propositions Run pricing and packaging experiments in collaboration with product and finance Optimize the demo → POC → close conversion funnel with structured tests and measurement Document findings in a shared experiment log to build institutional knowledge Tech Stack and Tools: You’ll be expected to work fluently across the following (or equivalent) tools: Category Tools CRM and Sales Engagement HubSpot (primary), Salesforce familiarity a plus Enrichment and Prospecting ZoomInfo AI and LLMs OpenAI APIs, Claude, custom AI workflows Data and Analytics SQL, Looker / Metabase / HubSpot reporting, Google Sheets Outreach and Sequencing HubSpot Sequences, Outreach, or equivalent Dev and Scripting Python, JavaScript/Node.js, REST APIs About You: 3+ years of experience in revenue operations, sales engineering, growth engineering, or a technical GTM role Hands-on proficiency building automations in CRM platforms (HubSpot strongly preferred) Working knowledge of APIs, webhooks, and integration platforms (Zapier, Make, or custom code) Experience implementing AI/LLM-powered workflows in a business context Strong analytical skills with the ability to build dashboards and interpret pipeline data Bias toward action: you ship fast, measure results, and iterate Excellent cross-functional communication — able to translate between sales, marketing, and engineering Experience in B2B SaaS, ideally selling into niche or vertical markets Background in the marina, attractions, hospitality, or venue management space Proficiency in Python or JavaScript for building custom tools and scripts Familiarity with Clay, Apollo, or similar enrichment and prospecting platforms Track record of running structured growth experiments with measurable outcomes Fluent in English, both written and verbal, is essential Legally authorized to work in Canada For information about DockMaster, please visit our website at www.dockmaster.com We thank all applicants for their interest; however, only those candidates selected for an interview will be contacted.