Director of Software Engineering

Department: Engineering

Employment Type: Full-Time

Location: Remote

About Us

At Bettermode, we are redefining how businesses streamline customer experiences and foster strong relationships. Our platform empowers businesses to seamlessly craft powerful web apps with engagement tools in its core tailored to their unique needs.

Backed by Silicon Valley investors and trusted by brands like Lenovo, Mercedes, and IBM, we’re proud to connect millions of end-users daily (check our Showcase page 😉).

Join us as we continue building tools that redefine customer engagement!

Benefits

• 🌟 At Bettermode, we’re dedicated to empowering our team to thrive—both professionally and personally. We offer location-based, competitive compensation that reflects your expertise and impact, with annual reviews so you can grow with us. Our culture is built on ownership and trust, giving you real influence over how we scale and succeed.
• 🩺 From your very first day, you and your family are covered by comprehensive Canadian health benefits—dental and vision included—so you can focus on what matters most.
• 😎 Enjoy unlimited paid vacation days, paid parental leave to support your family, and bereavement leave should you need it.
• 🛠️ You’ll have all the equipment you need provided, or you can bring your own device and access our Device Upgrade Policy—an interest-free hardware stipend repayable via payroll deductions, allowing you to upgrade when you need.
• 💡 We want you to thrive in your work: every team member receives a monthly Tech & Appreciation Stipend—perfect for testing new software or tools and improving your workflows as you see fit.
• 🏢 For in-person collaboration, our downtown Toronto office is less than a 15-minute walk from Union Station, with a free shuttle running throughout the day. The office features complimentary snacks, coffee, video games, and board games, as well as dedicated seating and a flexible environment that supports creativity, focus, and teamwork.
• 🌎 Join a globally diverse and collaborative team where you’re supported to do your best work and have access to all the resources needed to succeed.

About This Role

Employment Type: Full-time

Location: Toronto, Canada

Location type: Hybrid (3 days at the office in Downtown Toronto - Monday, Tuesday and Thursday)

Timezone: Eastern Standard Time

The Opportunity

We are looking for a Director of Software Engineering who has mastered the craft of coding and has now chosen to master the craft of Organizational Engineering.

You are a veteran of the industry (10+ years). You know what excellent code looks like because you used to write it. But today, you derive your satisfaction from building the machine that builds the product, not the product itself. You will lead our largest team, taking the operational weight off our Technical Leads and CTO so they can focus on architecture while you ensure the team runs smoothly

Responsibilities

• Own the "People Operating System": Manage the entire employee lifecycle for Backend and Frontend teams—hiring, 1:1s, performance reviews, and career ladders. You handle the "human friction" so our technical experts don't have to.
• Scale the Hiring Engine: Drive the pipeline from JD to onboarding. You will personally ensure we hit our aggressive headcount targets without lowering our high technical bar.
• Drive Velocity & Process: You own the shipping cadence. Using DORA metrics and agile principles, you identify bottlenecks and clear paths to ensure predictable delivery.
• Systematize AI-First Engineering: Make AI integration standard. You will embed tools like Claude Code, Cursor and LLMs into the SDLC, shifting the culture from "writing code" to "architecting and editing".
• Partner with Technical Leadership: You own the "Who" and "When" (Resourcing & Delivery); our Principal Engineers own the "What" and "How" (Architecture). You create the space for them to make high-level decisions by managing stakeholders and timelines.

What you bring to the team

We are not looking for a "professional manager." We are looking for a battle-hardened engineer who has mastered the art of leadership.

• Battle-Hardened Leader: 10+ years total experience with 3+ years in leadership. You have transitioned from being the best coder in the room to the person who builds the room.
• World-Class Communication & Presence: You possess impeccable articulation and the ability to frame narratives. Whether you are pitching a top-tier candidate, writing a delicate performance review, or reassuring an enterprise customer, your communication is crisp, persuasive, and nuanced.
• Technically Fluent: You can follow complex architectural debates and spot risks immediately, but your focus is on resources and feasibility rather than implementation details.
• Scale-Up Veteran: You have navigated the $5M to $20M ARR journey and know how to implement just enough process to create order without killing the startup spirit.
• Ego-Free: You are comfortable managing engineers who are technically stronger than you are today, measuring success by their output.

If you think this role is right for you, apply today! We’re excited to share more details, learn about your experience, and discover together if we’re the perfect fit for each other.

Commitment to Diversity

As we continue to grow with customers and team members worldwide, we are committed to cultivating an environment where everyone’s unique perspectives are heard and valued. The diversity of our team will enable us to build the most inclusive product and workplace possible. We encourage applications from all backgrounds, identities, abilities, and life experiences.

Additional Information

• Headcount: This is a vacancy at Bettermode.
• Compensation Range: Compensation for this role is expected to exceed CA$200,000 annually.
• AI Use: Large Language Models (LLM) might be used in the hiring process for this position to screen, assess or select job applicants.