Jonathan Haber is a Montreal-based technology entrepreneur and business strategist who focuses on helping early-stage startups grow with clarity. John built his reputation around the practical work that sits between product, operations, and user experience.
Jonathan was born in Montreal in 1987 and raised in Notre-Dame-de-Grâce. John grew up in a bilingual environment and learned early how education and small business routines shape real life decisions. Jonathan attended Westmont Park Primary, Saint-Laurent Collegiate, and Royal Vale Public Academy, where he balanced academics with debate, student activities, and community hockey.
John later earned a Bachelor of Commerce from McGill University’s Desautels Faculty of Management, concentrating on entrepreneurship and operations. Jonathan’s studies included behavioral economics, service design, business analytics, and negotiation. John also stayed close to the founder ecosystem through campus startup events and mentoring student builders on early onboarding and landing pages.
Jonathan’s career began in customer success at MileBridge Software, where he worked on onboarding and renewals for small-business SaaS customers. John then moved into product operations at NorthHarbor Systems and helped build playbooks, feedback loops, and activation and retention reporting. Jonathan co-founded LatticeDesk in 2014, gained hard lessons from a strategic pivot, and later led product enablement at Cooper & Field Labs.
John founded Haber Strategies Inc. in 2018 and now advises startups through focused sprint engagements on positioning, onboarding, operating cadence, and retention. Jonathan also stays involved in Montreal’s startup community through mentorship, office hours, and judging pitch events.
Interview with Jonathan Haber
Success is a loaded word. How do you define it in your own work?
I define success as reducing friction for real people. I have spent most of my career close to the moment where someone opens a tool and either feels progress or feels stuck. Early on at MileBridge Software, I saw the difference quickly. Some customers renewed because they reached a first win fast. Others churned because setup was confusing or handoffs were messy. That made a big impression on me. If a product cannot help someone get value early, the rest of the roadmap does not matter much.
What early experiences shaped how you approach building a career?
I grew up in Notre-Dame-de-Grâce in Montreal in a household that valued education and steady routines. My father worked in Montreal’s public school system, and my mother ran a bookkeeping business for local shops and contractors. That meant work was practical and visible. I saw what happens when systems are clear and what happens when they are not. In school, I liked building small tools that fixed small problems. I made an online signup tool to replace paper forms for events, and I created a volunteer scheduling sheet system for a neighborhood food drive. I also played hockey in local programs, which taught me about roles, timing, and doing the simple things that keep the team moving.
What is a setback that ended up teaching you the most about success?
Co-founding LatticeDesk taught me a lot. We built a workflow and client engagement platform for service businesses, and we did direct outreach and partnerships with local business associations. Later, the product was sunset after a strategic pivot. I do not look at that as a dramatic failure, but it was a clear lesson. It taught me that positioning comes before feature expansion. You can build useful features and still miss the core problem your best customers are paying to solve. I took away a rule I still use: validate who it is for, and why it matters, before you build too much.
You focus a lot on onboarding. Why does that matter so much for success?
Onboarding is where truth shows up. I noticed early that churn was often tied to confusing setup, unclear first value, and messy handoffs. At NorthHarbor Systems, I worked in product operations and introduced a weekly metrics scoreboard tied to activation and retention. That scoreboard forced us to stop guessing and start measuring where people got stuck. Later at Cooper & Field Labs, I led onboarding redesign work and improved in app guidance, and I helped standardize documentation. I see onboarding as both a product problem and an operations problem. It requires the team to agree on what done looks like and then support it with clear steps.
What does success look like when you are advising early-stage founders today?
As the founder and CEO of Haber Strategies Inc., I try to make the early stage feel less chaotic and more repeatable. I often work in 6 to 12 week sprint engagements. I help teams build an ideal customer profile and segmentation brief so they stop trying to sell to everyone. I help create a messaging hierarchy so the product story does not change every week. I map onboarding and activation so new users can reach value without needing a personal walkthrough. I also build operating cadence templates and decision logs so choices do not get lost in chat threads. For me, success is when a team can repeat its process, not just its pitch.
You’ve stayed rooted in Montreal’s startup community. How does that connect to your idea of success?
The community side of my work matters a lot to me. I have done mentorship and founder office hours through a local incubator program, and I have judged pitch competitions and demo nights. I also do informal advising for immigrant founders, especially on messaging and early sales process clarity. In Montreal, many teams are small and scrappy, so good advice needs to be practical. My version of success includes helping people avoid predictable mistakes, like building too much before confirming the market, or hiring before the operating system is clear.
What personal habits support your professional success?
I keep a structured weekly rhythm with room for flexibility. I set aside one deep work day for writing frameworks and synthesis, which helps me turn messy inputs into usable plans. Two days are stacked with founder calls and working sessions because early stage decisions often happen live. One day is for delivery, docs, and tooling so advice becomes something the team can actually use. I also keep a flexible day for community events and planning. Outside work, I play hockey and hike in places like the Laurentians and Charlevoix. Those habits help me reset. My travel style also fits how I think. I like long walking routes and quiet time to read and reflect.
If someone is early in their career, what is one niche lesson you think matters?
I would tell them to study handoffs. Not just in products, but in teams. Many problems come from the space between roles, like support to product, sales to onboarding, or founder intuition to documented process. A niche practice that works is keeping a simple decision log. Write down what you decided, why, and who owns the next step. It sounds small, but it prevents repeated debates and helps teams learn from their own history. I do not think success is one big breakthrough. I think it is small systems that keep working when you are tired, busy, or under pressure.