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About the role

  • GTM Engineer automating sales operations and building AI-driven systems for Dockmaster's revenue processes. Collaborating with cross-functional teams in a remote work model.

Responsibilities

  • 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
  • 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 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
  • 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
  • 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

Requirements

  • 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.

Job type

Full Time

Experience level

Mid levelSenior

Salary

Not specified

Degree requirement

No Education Requirement

Tech skills

ApolloJavaScriptPython

Location requirements

RemoteCanada

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