Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sits down with Leigh Sevin, co-founder and CEO of Endear, to examine how retail brands can bridge the gap between physical and digital sales through scalable clienteling.
Retail stores convert at 30% or more once a customer walks in. E-commerce converts at less than 1%. The math is not close. Yet most retail brands have built their entire growth strategy around the weaker channel — because the stronger one has a problem no one solved until recently: a physical store has no way to influence who walks through the door.
Leigh Sevin built Endear to fix exactly that. Since launching in April 2019, she has led Endear to become the only Shopify Plus certified clienteling application, powering sales for brands including Todd Snyder, Rebag, and Frame. When a store can identify a high-value customer who lives three miles away and has items abandoned in their online cart, and then have a store associate send a personal message inviting that customer in — that is the top-of-funnel control physical retail never had. That is what Endear does.
This episode is for CEOs of scaling retail and commerce brands who are trying to turn their physical stores into a repeatable, measurable growth engine instead of a costly bet on foot traffic.
Key Takeaways
- Physical retail outperforms e-commerce on every post-visit metric — 30%+ conversion rates, sub-4% return rates, higher average order values — but stores cannot influence their own traffic without a dedicated outreach tool.
- The biggest integration decision for a retail SaaS platform is not which tools to connect — it is correctly separating need-to-have integrations (transaction data, omni-channel purchase history) from nice-to-have integrations (existing marketing and support stacks).
- At Endear, the periods when Leigh Sevin had to step away completely — her honeymoon and parental leave — became the moments the team performed at its highest level, because removing the founder’s ability to second-guess created real, measurable empowerment.
- Selling into retail brands requires selling to the right buyer: digital buyers are flooded with solutions, while physical retail buyers are starved for them and have more to gain from a needle-moving platform.
- An internal AI culture is not built by mandate — Endear ran a company-wide AI challenge in Q4 where every employee had to solve a real operational problem using AI, present it to their department, and compete to present to the whole company.
How Retail CEOs Lose Sales by Failing to Control Physical Store Traffic
The blind spot Sevin sees most often in retail brands is not a product problem or a pricing problem. It is an organizational one. Most brands are not unified across digital and physical channels. They are separate teams, often with separate buyers, separate KPIs, and separate relationships with vendors.
That separation costs them money in a very specific way. Physical stores produce exceptional results once a customer is present. But the store itself — unlike a website — has no mechanism to drive who shows up. “The store itself has no way to influence traffic,” Sevin says. “So the only way you’re hitting any of those numbers is by relying on sheer luck of who decides to walk in.”
Glenn Gow, interviewing Sevin on The Scaling Executive Podcast, identified this as the core distinction that separates brands who treat physical retail as a fixed cost from those who treat it as a scalable growth lever. The question is not whether to invest in stores — the ROI metrics make that case on their own. The question is whether the CEO has given the store team a tool to generate its own demand.
Endear’s answer is to put that tool in the hands of store associates: the people who already know the customers, already have relationships with them, and already know what is in stock. What they have lacked is a system that tells them who to contact, with what information, at the right moment. “Even if their conversion rate was a hundred percent,” Sevin explains, “if only four people decided to walk in that day, even at a hundred percent, they’re not hitting their sales goals.”
The AI-assisted version of this Sevin is building toward takes the logic further. When a high-value customer who lives within three miles of a store abandons an online cart, the system surfaces that signal to the associate and offers to send a personal message on their behalf, inviting the customer to try those items in person. The combination of digital intent data and physical proximity — acted on by a human associate rather than a generic email — produces exactly the kind of outreach that turns a passive digital signal into a store visit.
How Scaling SaaS CEOs Decide Which Integrations to Build First
Endear sits at the intersection of multiple existing tools — point-of-sale systems, email marketing platforms, SMS tools, customer support software. Getting the integration strategy right was not optional. Get it wrong and the platform creates confusion for brands already managing a complex tech stack. Get it right and Endear becomes the connective layer that makes the rest of the stack more useful.
Sevin’s framework for making those decisions is simple and repeatable: separate need-to-have from nice-to-have, and build in that order.
Need-to-have integrations were defined by what Endear had to deliver before any other value was possible. “We needed transaction data,” Sevin explains. “We needed to be able to tell you the purchase history of a customer.” For many brands, Endear provided the first complete view of omni-channel purchase history they had ever seen — not just what a customer bought in one store, but what they bought across all stores and e-commerce combined. That total lifetime value across channels is the foundation for everything else: identifying VIPs, spotting discount shoppers, understanding who has purchased once versus a hundred times.
Shopify came first in that group, as the dominant omni-channel platform. Lightspeed and Square followed for physical retail transaction data.
Nice-to-have integrations were defined differently. They were not about what Endear needed to function — they were about what brands already had in place and needed Endear to respect. Klaviyo for email, SMS tools for text outreach, Gorgias for customer support. The first question brands asked after hearing about Endear’s POS integrations was always some version of: how does this work with what I already have? The integration strategy had to answer that question before it could move forward.
The lesson for any scaling SaaS CEO is that the integration roadmap is not a feature list — it is a trust-building sequence. Endear’s decision to prioritize Shopify first gave brands the omni-channel lifetime value view that became the platform’s core differentiator — the data layer that makes every subsequent integration more useful than it would be in isolation. You earn the right to be useful by solving the non-negotiable data problem first.
How Founders Scale Themselves as CEOs Without Losing Control of the Company
Sevin is direct about the tension at the center of every founder CEO’s job: the same instinct that makes you a good founder — wanting to be close to every decision — is the instinct that prevents your team from growing. “Learning to take your hands off and actually testing that,” she says, “is one of the biggest, most important things that a founder can do.”
The test she describes is not a planned delegation exercise. It is the forced absence. “Some of the times that my team have performed best is when I went on my honeymoon or when I went on mat leave, because my hands had to be off and they were very much off.” Without the ability to second-guess or redirect, the team made decisions on their own terms. The empowerment was not a gift — it was the removal of an obstacle.
Gow, drawing on his work coaching scaling executives, frames this as a values problem as much as a management problem. The CEO who does not know every employee on the team has only one reliable tool for ensuring good decisions get made without them: the values the company has built and communicated from the top down. “If you can get hiring right,” Sevin adds, “a lot of other things are going to flow naturally from there.” The right talent embraces the culture. The wrong talent resists it or dilutes it, regardless of how closely the CEO watches.
Sevin and co-founder Michael Fender have chosen to stay deeply involved in hiring as the company scales — not because they distrust the team, but because hiring is the point at which culture is either protected or compromised. “We really believe that if you bring on the right talent, those people will be open to that culture and those values and they’ll embrace them.”
How Retail SaaS CEOs Build an Internal AI Culture That Produces Real Results
Endear’s internal position on AI is not a policy — it is a practice. Sevin describes the company as “very firm, big believers” in AI’s ability to enhance how every employee does their work. The framing she uses to explain why is worth noting: “Usually it’s a trade-off between time versus quality. With AI, it’s both. You’re saving time and you’re increasing quality.”
That belief is only useful if it produces behavior. Sevin’s approach to turning belief into behavior was a company-wide AI challenge in Q4. Every employee had to identify a real operational problem in their day-to-day work and solve it using AI. They presented the solution to their department. The department voted on its favorite. The winner presented to the whole company — showing exactly what they built, how it worked, and how others could use the same approach.
The structure matters. The challenge did not ask employees to explore AI in general or attend a training session. It asked them to solve something real and then teach others how to replicate it. That is a different request — and it produces a different kind of cultural commitment.
On the product side, Sevin’s vision for AI is equally concrete. The goal is not to automate clienteling — it is to remove the friction that prevents store associates from doing the clienteling they already know they should be doing. Human error and human laziness, as she puts it, get in the way of the behavior that produces results. AI removes those obstacles: surfacing the right customer at the right moment, drafting the right message, and making it possible for the associate to act in seconds rather than minutes. “We really do believe in humans,” Sevin says. “We think that what we’re trying to do is facilitate conversations between really kind of high value, high potential customers and the store associates at the store. We just want to make it easier to surface who those people are.”
The Framework: What Leigh Sevin’s Scaling Decisions Produce
| Principle | What it means in practice | Named evidence from this interview |
| Control the top of funnel before optimizing conversion | A store with no traffic control cannot benefit from a strong conversion rate — fix top-of-funnel first | Endear was built to give physical retail teams the outreach capability that websites take for granted; brands like Todd Snyder and Frame now use it to drive measurable store traffic |
| Separate need-to-have from nice-to-have integrations | Build what you must have to deliver core value first; then earn the right to expand into the existing stack | Endear prioritized omni-channel transaction data via Shopify, Lightspeed, and Square before addressing coexistence with Klaviyo, Gorgias, and SMS platforms |
| Forced absence is the most honest test of organizational readiness | A CEO cannot evaluate whether their team is truly empowered while present to override decisions | During Sevin’s honeymoon and parental leave, Endear’s team made independent decisions at a level of quality and ownership Sevin credits as the company’s clearest proof that its hiring and culture model works |
| Make AI cultural through challenge, not mandate | Employees who solve a real problem with AI and teach others how to replicate it build durable AI fluency; employees who attend training sessions do not | Endear’s Q4 company-wide AI challenge required every employee to identify a real operational problem, solve it with AI, and present it — producing team-generated use cases rather than top-down directives |
Quotes from This Episode
- “Done is better than perfect. The only thing that determines if something is right is whether the people you’re targeting want it or like it.” — Leigh Sevin, Co-Founder and CEO, Endear
- “Even if their conversion rate was a hundred percent, if only four people decided to walk in that day, even at a hundred percent, they’re not hitting their sales goals.” — Leigh Sevin, Co-Founder and CEO, Endear
- “Learning to take your hands off and actually testing that is one of the biggest, most important things that a founder can do.” — Leigh Sevin, Co-Founder and CEO, Endear
- “We really believe that if you bring on the right talent, those people will be open to that culture and those values and they’ll embrace them.” — Leigh Sevin, Co-Founder and CEO, Endear
- “We really do believe in humans. We think that what we’re trying to do is facilitate conversations between really kind of high value, high potential customers and the store associates at the store. We just want to make it easier to surface who those people are.” — Leigh Sevin, Co-Founder and CEO, Endear
Frequently Asked Questions
Why are retail store sales teams losing revenue they could be capturing from their existing customer base?
Most retail brands have separated their digital and physical teams — different buyers, different KPIs, different vendor relationships — which means no one owns the full picture of a customer’s behavior across both channels. Leigh Sevin, co-founder and CEO of Endear, identifies this as the structural reason stores lose revenue they could capture: the store associates who have the deepest customer relationships have no system telling them who to contact, with what information, or when. Clienteling — using structured omni-channel customer data to drive personalized outreach — is the practice that closes that gap, and physical retail’s 30%+ in-store conversion rate means the upside of fixing it is significant.
How should a retail CEO decide which software integrations to prioritize when building a commerce tech stack?
Leigh Sevin’s framework at Endear is to separate need-to-have integrations from nice-to-have integrations and build in that order. Need-to-have integrations are those required to deliver the platform’s core value — for Endear, that meant omni-channel transaction data via Shopify, Lightspeed, and Square before anything else. Nice-to-have integrations are those that allow the platform to coexist cleanly with tools already in the brand’s stack, such as Klaviyo or Gorgias. The rule is: earn the right to expand by solving the non-negotiable problem first.
How do founder CEOs maintain company culture and decision quality as the team scales beyond their direct oversight?
Leigh Sevin argues that the most honest test of organizational readiness is forced absence — periods when the CEO genuinely cannot intervene. At Endear, the team performed at its highest level during Sevin’s honeymoon and parental leave, because the removal of second-guessing created real empowerment. To sustain that at scale, Sevin and co-founder Michael Fender stay deeply involved in hiring, operating on the principle that the right talent will embrace the culture and values the company has built, allowing decisions to be made well without direct oversight.
CEOs Work with Glenn Gow to Scale Their Companies by Scaling Themselves First
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
