Transparent Search Group
Forward Deployed Engineer
About the role
Company: Confidential - Well-funded vertical-software holding company
Location: Toronto, ON (also hiring in New York and San Francisco) - hybrid: minimum 3 days per week in office (4 preferred), plus 2-3 days per week of travel to portfolio company sites
Compensation: CA$180,000 - CA$260,000 base + competitive equity
Employment Type: Full-time
About the Company
A software holding company run by technology entrepreneurs that buys, builds and permanently holds vertical-market software businesses, embedding engineers with its portfolio companies to modernize them with AI.
The Role
This is a Palantir-style Forward Deployed Engineer role at a software holding company. You will embed directly with the company's portfolio companies, ship agentic software into their live operations, and own the outcomes end to end. You will not be writing decks. You will be building running systems, and because the company scales through software rather than headcount, what you build for one company is reused across every company in the same vertical.
From day one you will be the technical face of the company to portfolio company general managers, with high-leverage scope and real influence on how the whole company grows.
What You Will Do
- Embed with portfolio companies to understand their operating model, earn operator trust, and identify the two or three highest-leverage workflow opportunities for agentic software.
- Ship the wedge: build integrations, prompts, evals and UI surfaces to land the first agentic workflow at each company on the company's core platform.
- Operate and tune deployed systems after launch, adjusting levels of autonomy and handing off cleanly to portfolio operations once they are stable.
- Serve as the company's technical face to portfolio company GMs: build trust, set expectations, and make sure the system is seen as their leverage.
- Bring patterns back to headquarters and turn what you learn into reusable playbooks that speed up every future deployment in the same vertical.
What You Bring
- 3-6 years of experience in full-stack, customer-facing software or product engineering, or forward deployed engineering. 4-6 years with a mix of larger-company and startup experience is ideal.
- Full-stack proficiency: TypeScript or Python on the backend, React on the frontend, and SQL. You can own delivery end to end on your own.
- Experience shipping production LLM or agentic software to real users, with evals, autonomy gating and outcome tracking, not just demos or prototypes.
- Prior embedded or customer-facing engineering experience, such as a forward deployed, solutions or deploy-and-operate role.
- Operator instincts: you can read a P&L, turn ambiguous business problems into scoped technical solutions, and quickly earn the trust of non-technical stakeholders.
- Strong executive presence and polished communication with C-suite leaders and GMs.
- Daily use of AI development tools and agents to automate your own work.
- A consistent track record with meaningful tenure and growth in your roles.
- Comfort with frequent travel to portfolio company sites (2-3 days per week).
Nice to Have
- Experience at a recognizable early-stage or high-growth startup
- Exposure to private equity, consulting, or vertical SaaS operating environments (portfolio operations, M&A integration or similar)
- Founder or founding-engineer background
- Programming experience in Go
Interview Process
Recruiter screen (30 min), technical screen (30 min), 2-hour AI take-home project, take-home follow-up (30 min), then a combined system design and experience/values interview (45 min).
Tech Stack
TypeScript, Python, React, SQL, LLMs and foundation models, agentic workflows, evals, Snowflake, Databricks, Apache Iceberg, event-driven systems
Your application is reviewed by a TSG search consultant.
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