Technical Lead Manager

June 22, 2026

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<div class="content-intro"><h4>This is a 100% remote position open only to candidates currently based in Canada. Applicants must be legally authorized to work in Canada and reside in the country.</h4> <h3> </h3> <h3>About Point</h3> ✨ Real Impact, Real People: Our mission at Point is to make homeownership more valuable and accessible. Your work directly helps homeowners access their wealth, achieve financial flexibility, and realize life changing goals. ✨ Funding: With over $175M raised from top investors like Andreessen Horowitz, WestCap, Greylock, and Prudential, we’re scaling fast! You have the opportunity to join us at a pivotal stage. ✨ Game-changing Product: We're building a category defining company in home equity. We’ve earned a 4.7 Trustpilot rating and an A+ from the BBB, a testament to the value we provide to our 20,000+ customers. ✨ Great Place to Work: Our employees love working here! We are a <a href="https://www.greatplacetowork.com/certified-company/7037273">Certified Great Place to Work and a Fortune Best Workplaces in the Bay Area</a>. ✨ Remote First Culture, Genuine Connection: Work from anywhere in Canada while staying closely connected through virtual collaboration, team gatherings, and a people-first culture. </div>About the role AI is reshaping how we serve homeowners at Point — from voice agents to email, chat, and SMS agents that enable self-service at scale. We're hiring a Technical Lead Manager to lead the team building them. You'll run a small, senior team, stay hands-on in the code, set technical direction, and work directly with Product, Ops, and CX. If you want to ship applied AI that customers directly interact with, this is the role. Check out our latest <a href="https://point.com/blog/engineering-wins-at-point-in-2024" target="_blank">Engineering Blog</a> to learn more about why it's a great time to join Point's Engineering team! Your responsibilities <ul> <li>Define the AI technical strategy for CX, including evaluating and selecting frameworks, platforms, and vendor solutions.</li> <li>Own the technical roadmap for Point's AI-powered customer experience — voice, email, chat, and SMS agents that handle real homeowner interactions.</li> <li>Write code alongside your team — review PRs, prototype new agent capabilities, and debug production issues.</li> <li>Partner with Product, CX, and Ops to identify where AI agents can replace or augment manual workflows, then ship it.</li> <li>Establish success metrics for agent performance and use data to prioritize the roadmap.</li> <li>Design reliable agent architectures — orchestration, tool use, guardrails, fallback handling — that work at production scale.</li> <li>Lead and grow a small, senior engineering team: set high expectations, remove blockers, create space for deep work.</li> <li>Drive observability and reliability across the AI agent stack, leveraging tools like Langfuse.</li> </ul> About you <ul> <li data-section-id="mqwnvj" data-start="104" data-end="259">7+ years of software engineering experience building and operating production systems, including at least 2 years leading or managing engineering teams.</li> <li data-section-id="k20cx0" data-start="260" data-end="383">Proven experience developing and shipping LLM-powered, conversational AI, or agentic systems in real-world environments.</li> <li data-section-id="vwqk7g" data-start="384" data-end="517">Track record of delivering customer-facing products end-to-end, from initial design through deployment, monitoring, and iteration.</li> <li data-section-id="1brebrh" data-start="518" data-end="700">Strong ability to partner with cross-functional stakeholders (Product, Operations, CX) to translate business needs into scalable technical solutions and deliver measurable impact.</li> <li data-section-id="1eme8xo" data-start="701" data-end="801">Deep systems design expertise, with a focus on building reliable, observable, real-time services.</li> <li data-section-id="fu4ik3" data-start="802" data-end="941">Demonstrated technical leadership, including guiding architecture decisions, evaluating trade-offs, and ensuring high-quality execution.</li> <li data-section-id="x2knjy" data-start="942" data-end="1086">Experience defining and driving technical strategy and roadmaps for AI-driven, agentic customer experiences aligned with business objectives.</li> <li data-section-id="1emffe" data-start="1087" data-end="1239">Proven ability to hire, mentor, and develop high-performing engineering teams, fostering a culture of ownership, innovation, and continuous learning.</li> <li data-section-id="1miqhkg" data-start="1240" data-end="1364">Experience managing and mentoring engineers, driving performance, and building a strong, accountable engineering culture.</li> <li data-section-id="1abtfiu" data-start="1365" data-end="1496">Hands-on experience with LLM and agent development, including prompt engineering, RAG, tool usage, and orchestration frameworks.</li> <li data-section-id="xyjtv1" data-start="1497" data-end="1602">Comfortable making build-vs-buy decisions and rigorously evaluating third-party vendors and platforms.</li> <li data-section-id="jezz1s" data-start="1603" data-end="1730">Familiarity with conversational AI infrastructure such as telephony, messaging APIs, or chat platforms at scale (preferred).</li> <li data-section-id="tr81bl" data-start="1731" data-end="1881">Experience with AI/ML evaluation and observability, including instrumentation for quality, drift detection, and continuous improvement (preferred).</li> <li data-section-id="nyac0d" data-start="1882" data-end="2002" data-is-last-node="">Bachelor’s or Master’s degree in Computer Science, Engineering, or a related field, or equivalent practical experience.</li> </ul> Compensation at Point will be determined by skills, experience, and geographic location. <ul> <li>188,080 - 207,878 CAD</li> </ul> This does not include any other potential components of the compensation package, including equity, benefits, and perks outlined above. At the launch of each position, we benchmark compensation to the appropriate role and level utilizing competitive compensation data from various data sources as references. At the offer stage, we use the signal we received from our interviews, coupled with your experience, location, and other job-related factors, to determine final compensation.<div class="content-conclusion"> Point is proud to be an equal-opportunity employer. We provide employment opportunities regardless of age, race, color, ancestry, national origin, religion, disability, sex, gender identity or expression, sexual orientation, veteran status, or any other protected class. Each individual at Point brings their own perspectives, work experiences, lifestyles, and cultures with them, and we believe that a more diverse team creates more innovative products, provides better services to customers, and helps us all grow and learn. <a href="https://point.com/cpra-hr-applicant-privacy-notice" target="_blank">California Consumer Privacy Act Notice</a></div>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...