GTM Engineer - DockMaster

DockMaster Software is the leading marina management platform serving entertainment attractions and venues across the waterfront industry. The GTM Engineer will design and maintain the technical infrastructure that powers Dockmaster’s revenue engine, automating and optimizing sales and marketing operations while collaborating cross-functionally with various teams.

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
• 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
• 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
• 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 the US