Staff Software Engineer leading frontend system initiatives at a fintech company. Influencing architecture and mentoring team members to enhance code quality.
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.
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