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
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