Staff AI Operations Lead

Location: Canada What We’re Building Honeycomb is a service for the near and present future, defining observability and raising expectations of what developer tools can do! We’re working with well known companies like HelloFresh, Slack, LaunchDarkly, and Vanguard and more across a range of industries. This is an exciting time in our trajectory, we’ve closed Series D funding, scaled past the 200-person mark, and were named to Forbes’ America’s Best Startups of 2022 and 2023! If you want to see what we’ve been up to, please check out these blog posts and Honeycomb.io press releases. Who We Are We come for the impact, and stay for the culture! We’re a talented, opinionated, passionate, fiercely inclusive, and responsible group of bees. We have conviction and we strive to live our values every day. We want our people to do what they truly love amongst a team of highly talented (but humble) peers. How We Work We are a fully distributed company, which means we believe it is not where you sit, but how you deliver that matters most. We invest in our people and care about how you orient to our culture and processes. At the same time we imbue a lot of trust, autonomy, and accountability from Day 1. About the problem space AI has changed what's possible in go-to-market, support, and business operations. The constraint is no longer "can we build it" — it's "can we deploy it into a real workflow, prove it made things better, and keep it working." Most companies are stuck at the demo stage: a lot of clever prompting, very little that runs reliably on Tuesday morning without someone watching it. This role exists to get us past that, everywhere outside of engineering. Little more about the team: You'll sit on the Data team, which is where this work belongs. Our team already operates at the seam between the business and its systems — we partner daily with RevOps, Customer Success, Sales, and Product, and we own the data infrastructure these workflows depend on. AI-in-the-business is a data problem with a model attached, and you'll have the pipelines, the warehouse, and the domain relationships already in place. What you'll do You are a senior individual contributor. Your job is to take business workflows that are slow, manual, or inconsistent, and make them fast, automated, and measurably better — then do it again, and leave behind enough shared scaffolding that the third one is easier than the first. Ship automated workflows end to end Partner with department leaders to identify the highest-leverage workflows in their orgs, and go deep enough on how the work actually happens to know where a model helps and where it doesn't. Define success before you build: cycle time, quality, cost, risk. Instrument it. Report on it honestly, including when the answer is "this didn't work." Deliver working systems, not prototypes, with evaluation harnesses, human-in-the-loop review where the stakes call for it, and ongoing monitoring. Iterate on adoption the way a product manager would: user research, documentation, and a real plan for getting people to use the thing. Build the shared substrate as you go Establish patterns for model access, orchestration and agents, prompt and tool management, evaluation, logging, and cost control — derived from what real workflows needed, not designed in advance. Build on the Data team's existing infrastructure rather than standing up parallel systems. Co-own shared components with your counterpart in Engineering; identify dependencies early and bring them into partner roadmaps collaboratively. Make the company fluent Create templates, playbooks, and golden paths: prompt patterns, agent patterns, safety checklists, evaluation patterns. Run office hours, demos, and community-of-practice sessions that make adoption feel accessible rather than intimidating. Develop enablement material for distinct audiences — GTM, operations, leadership — from fundamentals through advanced workflows. Help people build judgment about AI: when to use it, when not to, and how to tell whether it worked. Keep it safe and governable Partner with Security, IT, and Legal on access control, data handling, vendor risk, and policy — so that employees have a clear, fast, safe path to experiment. Work with the Data team to apply our data classification standards to AI use cases: what data can be used for retrieval and context, and what audit trails are required when sensitive data flows through LLM pipelines. What you'll bring Deep experience shipping systems into real business workflows — you've owned something end to end, in production, that non-technical people depended on daily. Hands-on fluency with modern AI stacks: LLMs, retrieval, tool use and agents, evaluation, guardrails — plus the pragmatism to keep things shippable. The ability to learn someone else's job well enough to improve it. This role lives or dies on understanding how support, sales, or finance actually work. A track record of leading cross-functional initiatives without formal authority, bringing clarity, momentum, and crisp decision-making. Comfort navigating security, privacy, and compliance tradeoffs in real organizations: data classification, retention, access controls, vendor risk. Strong teaching instincts — you explain complex things simply, write clear docs, and meet people where they are. Demonstrated ability to stay current as the landscape shifts, and to change your mind in public when the evidence does. Nice to have SQL fluency and comfort in a modern data stack (dbt, a cloud warehouse, BI tooling). Experience with workflow automation or enterprise systems: case management, ticketing, CRM, knowledge bases. Familiarity with observability practices for AI systems: monitoring, quality signals, evaluation pipelines, cost and latency analysis. Change management experience across a distributed, multi-function company. Interest in external evangelism — writing, speaking, podcasts, peer groups. Base Salary based on level of experience $310,000—$360,000 CAD What you'll get when you join the Hive: A stake in our success - generous equity with employee-friendly stock program It’s not about how strong of a negotiator you are - our pay is based on transparent levels relative to experience Time to recharge with unlimited PTO A distributed-first mindset and culture (really!) Home office, co-working, and internet stipend Full benefits coverage for employees, with additional coverage available for dependents Up to 16 weeks of paid parental leave, regardless of path to parenthood Annual development allowance And much more... Please note we cannot currently sponsor or support visa transfers at this time. Additionally, in compliance with applicable law, all persons hired will be required to verify identity and eligibility to work. Phishing and Recruitment Scam Warning: We take your security seriously. Please be aware that recruitment scams are increasingly common and scammers may create email addresses or websites to impersonate Honeycomb employees. To help protect you: All communications will come from an @honeycomb.io email address We occasionally work with external recruiting agencies. These partners will use legitimate business email addresses— never personal accounts like Gmail or Yahoo . Our recruiting process will never ask you to provide financial or sensitive personal information, including but not limited to: Social security or tax identification numbers Credit card numbers Bank account information Diversity & Accommodations: We're committed to building a diverse, inclusive, and equitable workplace—where people of all backgrounds, identities, experiences, and abilities are welcomed, valued, and supported. We recognize that there is no single path to success and embrace nontraditional career journeys and diverse perspectives as key to building stronger, more innovative teams. We strive to ensure an inclusive experience throughout every stage of our hiring process and are happy to provide reasonable accommodations as needed. If you require accommodations or accessible formats at any point during our hiring process, please let your recruiter know. As an equal opportunity employer our hiring process is designed to put you at ease and help you show your best work. If there’s anything we can do to improve your experience, we’re always open to feedback. Privacy Notice: If you apply for a job at Honeycomb and your application is unsuccessful (or you withdraw from the process or decline our offer), Honeycomb will retain your information after your application for a period of time in accordance with local laws. We retain this information for various reasons, including in case we face a legal challenge in respect of a recruitment decision, to consider you for other current or future jobs at Honeycomb, and to help us better understand, analyze and improve our recruitment processes. For more information regarding our privacy practices please see the Honeycomb Privacy Notice. If you do not want us to retain your information, or want us to update it, please contact . Please note, however, that we may retain some information if required by law or as necessary to protect ourselves from legal claims.