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Principal Engineer (AI, Office of the CEO)

Jobber · Boston, United States

About this role

Jobber seeks a founding AI engineer for a small team in the Office of the CEO. Reporting to the VP of Customer Experience Innovation, this person will build internal AI systems from initial design through production to change how teams across the company work. The role combines hands-on engineering with direct collaboration with functional and executive leaders.

Responsibilities

  • Architect and deliver production AI systems using LLMs, retrieval, agents and integrations, with pragmatic technical foundations.
  • Establish standards for trustworthy AI at company scale, including retrieval quality, permissions, security and reliability.
  • Embed with teams to put AI into their workflows, then leave behind maintainable systems and clear owners. Work with function leaders day to day and executive leadership weekly.
  • Evaluate build-versus-buy options, run rapid proofs of concept and make decisions about which approaches to pursue. Deliver working systems that inform company decisions.

Qualifications

  • A record of building production systems at Staff+ scope, such as data infrastructure, retrieval or applied AI used daily by hundreds to thousands of people. No minimum number of years or education requirement is stated.
  • Hands-on depth with the modern AI stack, experience seeing how AI systems can be confidently wrong, and a daily working relationship with AI tools and agents.
  • Founding-engineer, consulting or forward-deployed experience; pragmatic technology judgment; ownership of outcomes in other teams’ domains; and the communication skills to explain technical decisions to a CEO. The role calls for shipping every few weeks without compromising trustworthiness.

Location and compensation:

The application lists Boston and labels the location type Remote, but explicitly limits the role to candidates based in the Boston area and requires office attendance at least one day per week. Candidates must be legally entitled to work in the US. Annual base salary is $229,300–$310,200, with a $269,700 midpoint. The stated package includes equity, health and wellness stipends, retirement savings matching, extended health coverage with fully paid premiums, and career development and coaching.

For full details about this role, click “Apply on company site” to view the employer’s original posting.

Skills for this role

AI systems architectureLarge language modelsRetrievalAI agentsSystems integrationData infrastructureAI securityAccess controlReliability engineeringProof of concept developmentBuild-versus-buy evaluationCross-functional collaborationExecutive communication

Your skill match

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Get interview-ready for this role

A focused preparation guide, built around this job’s responsibilities and requirements.

✦ AI-generated guide
Preparation suggestions, not the employer’s actual interview questions. Always check the original posting for current requirements.
01

Understand the role

What matters most

  • Build internal AI systems from design to production

    The founding engineer is responsible for end-to-end delivery across LLMs, retrieval, agents and integrations, using pragmatic foundations. For preparation, be ready to explain architectural choices and how a system moved from prototype to dependable daily use.

  • Set standards for trustworthy AI

    The role explicitly owns retrieval quality, permissions, security and reliability at company scale. Prepare to discuss concrete ways to detect confidently wrong outputs and protect access to information.

  • Put AI into real workflows

    The engineer will embed with functions, work day to day with their leaders and teams, and leave behind maintainable systems with clear owners. Prepare an example of translating a team’s workflow into a deployed system and transferring ownership.

  • Make fast technical and executive decisions

    The posting calls for build-versus-buy evaluations, rapid proofs of concept, decisions to stop unpromising work, and weekly work with executive leadership. Prepare to explain decision criteria and communicate technical trade-offs in business terms.

Likely challenges to think through

  • Shipping quickly without weakening trust

    A likely tension is delivering working AI every few weeks while maintaining the stated standards for quality and security. Prepare to describe how you would scope an initial release, test failure modes and decide what must be reliable before rollout.

  • Owning outcomes across team boundaries

    Embedding in another function may make it difficult to balance local workflow needs with reusable company-wide foundations and a durable handoff. Prepare to explain how you would agree on success measures, involve future owners and avoid leaving a system only its builder can operate.

  • Choosing when to stop a proof of concept

    Rapid build-versus-buy decisions may require abandoning a promising demo when it cannot meet production needs. Prepare criteria for comparing options on workflow fit, trustworthiness, integration effort and ongoing ownership; this is a preparation hypothesis, not a reported Jobber problem.

03

Practice your answers

Technical practice

How would you take a new internal AI system from initial design to production?

What to coverSuggested preparation: Describe how you would define the workflow, choose a pragmatic architecture, and establish production readiness. Explain how the design would change when people across multiple functions depend on the system.

How would you measure and improve retrieval quality?

What to coverSuggested preparation: Discuss representative queries, relevance checks, and how you would diagnose missing or misleading results. Explain the trade-off between improving retrieval and adding safeguards when the available information is insufficient.

How would you enforce permissions in an AI system that retrieves internal information?

What to coverSuggested preparation: Explain where access checks belong across retrieval and response generation, including what happens when a user cannot access a source. Address how you would test that the system does not reveal restricted information.

What security boundaries would you set for an AI system with integrations?

What to coverSuggested preparation: Discuss the data and actions an integration should be allowed to access, and how you would limit an agent’s authority. Explain how you would evaluate risks introduced by untrusted content or external systems.

How would you respond when an AI system gives a confident but wrong answer?

What to coverSuggested preparation: Trace whether the failure came from source data, retrieval, generation, or an integration. Explain how you would reduce recurrence and communicate uncertainty without making the system unusable.

How would you make an internal AI system reliable for daily use at company scale?

What to coverSuggested preparation: Identify the failures worth monitoring and how you would detect a decline in quality or availability. Discuss recovery and fallback choices in light of the impact on teams that depend on the system.

When would you use an agent rather than a simpler LLM workflow?

What to coverSuggested preparation: Compare the value of multi-step tool use with its added complexity, failure modes, and oversight needs. Describe how you would keep integrations and agent actions bounded by the workflow’s requirements.

How would you make a build-versus-buy decision for an internal AI capability?

What to coverSuggested preparation: Compare options against workflow fit, trustworthiness, integration effort, and long-term ownership. Explain what evidence would justify building something custom instead of using a proven option.

What would make you continue or stop a rapid AI proof of concept?

What to coverSuggested preparation: Define a narrow question the proof of concept must answer and evidence that would change the decision. Distinguish a promising demonstration from an approach that can meet production quality, security, and reliability needs.

How would you ship frequently without weakening technical standards?

What to coverSuggested preparation: Explain which trust and production checks you would treat as non-negotiable, and where you would deliberately limit scope. Discuss how you would leave a maintainable system with clear owners after embedding with a team.

Behavioural practice

Tell me about a time you owned a technical outcome in another team’s domain.

What to coverSuggested preparation: Use a real situation, your actions with the domain team, and the result. Explain how you learned their workflow without taking ownership away from them.

Tell me about a time you explained a consequential technical decision to senior leaders.

What to coverSuggested preparation: Describe the situation, how you presented the options and trade-offs, and the resulting decision. Show how you made the implications clear without hiding uncertainty.

Tell me about a proof of concept you stopped or substantially changed.

What to coverSuggested preparation: Give the original goal, the evidence you gathered, the action you took, and the result. Explain how you avoided continuing simply because work had already been invested.

Tell me about an AI or data system failure that changed your engineering approach.

What to coverSuggested preparation: Describe what happened, your specific response, and the result without overstating your role. Focus on what the failure taught you about quality or trust and what you changed afterward.

Tell me about a time you handed a system over to lasting owners.

What to coverSuggested preparation: Explain the situation, how you prepared the receiving team to operate and improve the system, and what happened after handoff. Distinguish a completed delivery from an outcome the team could sustain.

02

Sharpen your knowledge

Topics to prepare

  • End-to-end internal AI architecture

    Revision exercise (suggestion): Sketch two architectures for an internal workflow using LLMs, retrieval, agents and integrations; explain where you would favor simpler, proven components. The posting calls for pragmatic design from zero to production.

  • Trust boundaries and retrieval quality

    Revision exercise (suggestion): Map how source quality, user permissions and security affect what an AI system may retrieve and return. These are explicit company-scale responsibilities in the posting.

  • Confidently wrong AI outputs

    Revision exercise (suggestion): Analyze a hypothetical plausible-but-false answer, tracing its likely cause and deciding what evidence would justify showing it to a user. The posting specifically seeks experience with this failure mode and trustworthy systems.

  • Production reliability at Staff+ scope

    Revision exercise (suggestion): Outline the operational decisions for a system used daily by hundreds or thousands of people, including failure handling and maintainable ownership. That usage scale and production track record are stated in the posting.

  • Build-versus-buy judgment

    Revision exercise (suggestion): Define criteria for choosing, continuing or stopping a short AI proof of concept, and identify when a proven option beats a custom build. The role explicitly involves fast evaluations, POCs and defensible technology choices.

Skills to revise

  • Prototype a workflow integration

    Practice exercise (suggestion): Build a small, hypothetical internal workflow that connects retrieval and an LLM to an existing system, then document the path from prototype to production. The posting calls for hands-on work across LLMs, retrieval, agents and integrations; it does not prescribe a particular tool.

  • Test permissions and retrieval

    Practice exercise (suggestion): Create sample documents with different access levels, then test whether retrieval returns relevant material without exposing restricted content. This directly reflects the posting's retrieval-quality and permissions responsibilities.

  • Evaluate AI failure cases

    Practice exercise (suggestion): Assemble a small set of misleading or incomplete inputs, record where outputs are confidently wrong, and propose mitigations and release checks. The posting emphasizes trustworthiness while shipping frequently.

  • Run a bounded proof of concept

    Practice exercise (suggestion): Time-box a comparison of a custom approach and an existing option; produce a working demonstration, decision criteria and a clear stop-or-continue recommendation. The role requires rapid POCs and build-versus-buy decisions.

  • Hand off work and explain decisions

    Practice exercise (suggestion): Write an owner-facing handoff for the hypothetical workflow and a brief executive explanation of its value, risks and technical tradeoffs. The posting calls for embedding with teams, leaving clear owners and explaining decisions to a CEO.

04

Your preparation checklist

  • Select a Staff+ production-system walkthrough

    Prepare a diagram and concise account of a data, retrieval, or applied-AI system you built, if available. Show your decisions, production rollout, usage evidence, and outcomes; the posting seeks systems used daily by hundreds to thousands of people.

  • Practice an internal AI system design

    As a hypothetical exercise, sketch an LLM-based workflow from first design to production. Explain where retrieval, agents, and integrations help, and where a simpler, proven approach is preferable.

  • Document a trustworthy-AI failure and response

    Prepare an example, if you have one, of an AI system being confidently wrong. Explain how you detected it and what you changed to improve retrieval quality, permissions, security, or reliability.

  • Draft a build-versus-buy decision brief

    Compare two plausible approaches for a hypothetical internal AI need. Specify a small proof of concept, evidence needed to proceed, and criteria for stopping it; the role calls for fast evaluations and POCs.

  • Prepare a cross-functional handoff story

    Outline how you worked inside another team's domain, learned its workflow, shipped a useful system, and transferred ownership. Use a real example if available; Jobber emphasizes embedding with teams and leaving maintainable systems behind.

  • Rehearse a CEO-level technical update

    Practice a short explanation of a technical decision, its trade-offs, trust safeguards, and business impact. The role works with executive leadership weekly and calls for shipping every few weeks without compromising trustworthiness.

  • Bring focused questions for Jobber

    Ask which internal workflows are the first priorities, how AI standards and ongoing ownership will be set, and what would make an early POC worth pursuing. Clarify the Boston-area, at-least-one-day-per-week office requirement if relevant.

AI-generated from the job information · Prepared Sep 30, 2026 (UTC)Useful preparation, not a guarantee of eligibility or an offer.

Availability last checked: Oct 17, 2026. Status can change after a check; confirm on the employer’s website. Report an issue · Our checking policy

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