Icon
The Ebbs and Flows of Scaling a Startup with Loop CEO Jonathan Poma

The Ebbs and Flows of Scaling a Startup with Loop CEO Jonathan Poma

Adrian Alfieri
Adrian Alfieri
CEO, Verbatim

Jonathan Poma is the founder and CEO of Loop, an exchange-first returns platform for Shopify brands. We sat down with Jonathan to learn more about Loop’s origin, his shifting role, and how to hire – and retain – top talent in the ecommerce space.

Returns are a headache to process, both for brands and for customers. Until recently, there weren’t many tools that alleviated this problem – making matters even worse for scaling ecommerce brands. But thanks to Loop, returns are finally headache-free. 

Loop has redefined the post-purchase experience by enabling Shopify brands to transform returns into exchanges while automating their returns process. Over the last five years, they’ve supported brands like Allbirds, Figs, and Brooklinen retain more than $400 million in revenue.

We met with Jonathan Poma, Loop’s founder and CEO, to discuss what it’s like running a software business, where we covered: 

  • Finding product-market fit and early success
  • Remaining flexible while fundraising and scaling
  • Hiring and retaining top talent in the ecommerce space


Finding product-market fit and early success

As a previous consultant, Poma worked closely with Chubbies, where he noticed firsthand the challenges of manual returns processing. Using this as a catalyst, Poma started Loop with a colleague, Kyle Hency, and they both quickly realized Loop had exceptional product-market fit. 

Chubbies became their first client – and processing returns worked so well for them that Loop onboarded Allbirds as their next customer. From there, things took off.

Jonathan recalls how quickly Loop found product-market success, and how fast they hit a ceiling.

“Our business was propped up by product-market fit,” he said. “But, five years ago, we were still convincing people that returns actually meant something to their bottom line. We didn’t realize the scale of the opportunity until 2019.”

Although the business was generating revenue, growing 150-200% year-over-year, they had no lead generation or marketing functions, making their business hard to find.

"Early on, the only way people found us was by digging into the source code of the Allbirds returns website and finding loopreturns.com, then emailing us to get in touch," he said. “It was too challenging.”

It was time to mature the business, so Jonathan and his team:

  • Established a product vision and roadmap with clear goals
  • Brought on operators, allowing the founders to focus on the business
  • Hired sellers and marketers to develop go-to-market strategies


Remaining flexible while scaling and fundraising 

Evolving from a scrappy Columbus-based startup to a venture-backed, growth-stage company required a certain level of flexibility and foresight, both from Jonathan and his growing team.

“In 2020, the scale of ecommerce grew exponentially,” he said. “That’s when more merchants realized that returns and exchanges could be profitable – and that they needed our help to capture the opportunity.” 

The business began to grow, and by 2021, the competitive landscape shifted, positioning Loop as the market leader in the returns space. 

Loop went on to raise $65M in Series B funding during the summer of 2021, and Jonathan admitted that he and his team felt the pressure. “At the seed stage, investors believe in the idea,” he said. “At Series A, they’re investing in product-market fit. But, at Series B, they’re betting on you to scale beyond that.”

“There are some huge expectations that come after fundraising,” he said. “But the team and I were energized to scale Loop, and we seized the opportunity.”

Today, Loop supports over 1,100 of Shopify’s best brands, and Jonathan understands his shifting role comes with the territory.

Here are a few lessons Jonathan learned during this growth period:

  • You build trust by spending quality time with your team-members
  • You get the best out of your team by knowing what motivates them
  • You unleash your team's success by accepting that you're no longer the expert
  • Get past your ego; it's what is standing in the way of you and success


Hiring and retaining top talent in the ecommerce space

Part of successfully scaling a business includes hiring talented people – and Loop takes this responsibility seriously.

“Every week I reflect on whether to hire an external candidate or give an up-and-coming team member a chance to prove themselves,” he said. “There has to be a healthy mix of both internal promotions and external hires to create a balanced company culture.”

As a result, Loop leaders keeps these questions in mind while developing new roles: 

  • How does this align with our vision?
  • Are you building a job for yourself, a business, or an exit opportunity?
  • What level of capital do you have available to hire?
  • Will this person be an operator or a visionary?
  • Can we promote someone internally?

It’s one thing to promote or hire top talent, it’s another thing to retain them. “High performers play a vital role in the success of any organization,” he said. “But keeping them happy and engaged is entirely different.”

Jonathan believes four factors influence top talent to not only join, but stay, at Loop:

  • Constantly Learning: Team members need to constantly learn, or they’ll go elsewhere.
  • Vision Alignment: Team members need to believe in the company's vision.
  • Competitive Compensation: Team members need to be compensated competitively.
  • Company Culture: Team members need to see that company culture is thriving.

"I think the most important factor in employee happiness and business success is company culture,” he said. “I like to say that culture is the culmination of accepted, expected, and tolerated behaviors at a company, and that a good business is only as scalable as its culture."

Today, Loop employs over 130 team members across North America – and counting. Interested in working at Loop? Check out their careers page here.

Adrian Alfieri
Adrian Alfieri
CEO, Verbatim
ObviBackboneHiyaImmiMilaKitsch
info
Problem

Brainstorming 100 unique, 40-second scripts is painful.

Manually matching 20 clips (from your 10,000-video library) to each shot in your 100 unique scripts is even more painful.

Creating 10 permutations of each of the 100 ads (for A/B testing) is maximum pain.

Now imagine voiceovers, captions, music, & manually uploading all 1,000 ads to Meta & TikTok on top of this.

Products for scriptwriting (ChatGPT), competitor research (Foreplay), creative storage (Recharm, Air), editing (CapCut), creative analytics (Motion), & video production (Billo) exist, but they're not built for admaking (or just built badly).

Problem
Solution

Icon solves this with the first AI Admaker.

AI Admaker helps with scriptwriting, ad research, video creation, script-to-shot matching, permutations, voiceovers, captions, music, analytics, ad auto-launching, & more.

Solution

What they're saying

Obvi
"We went from spending hours making each ad to building entire campaigns in minutes. Icon's AI helps us shape perfect creatives at incredible speed."
Ron Shah

Ron Shah

CEO, Obvi

Products

Admaker(replaces CapCut, Adobe Premiere)

Create winning ads in minutes.

Uses AI for scriptwriting (AdGPT), video creation (A-roll, B-roll, UGC), script-to-shot matching (existing & AI-generated videos), permutations, voiceovers, captions, music, & more.

Replaces CapCut ($7.99/month), Adobe Premiere ($54.99/month)

Admaker
Adspy
(replaces AdSpy, Foreplay)

Save time with AI-powered ad cloning.

Replaces Foreplay ($49-$99/month + $20/user), AdSpy ($149/month)

Adspy
Ads Manager
(replaces Meta & TikTok Ad Managers)

Save time with ad manager auto-upload.

Replaces Meta & TikTok Ad Managers (direct use)

Ads Manager
Creative Library
(replaces Recharm, Air)

Save time by storing, tagging, creating, & splitting videos with AI.

Videos are used as building blocks for AI-generated ads in Admaker.

Replaces Recharm ($500-3K/month), Air ($250-$2K/month)

Creative Library
Creative Analytics
(replaces Motion)

Save money with built-in creative analytics.

Replaces Motion ($1K-$10K/month)

Creative Analytics
UGC Creators
(replaces Billo)

Save time & money with AI-generated UGC.

Replaces Billo ($99/video)

UGC Creators

Story

Kennan Davison

Kennan Davison

CEO, Founder
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
CPO, Chairman, Founder at Skio (CEO 2021-2024, $10M+ ARR in 3 years, profitable).
Previously: Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends Challenger (Top 200 North America, 100M+ players globally), Y Combinator S20 (solo founder), Columbia (transfer, dropout).
Hi, I'm Kennan!
Growing up, my dream was to be a pro gamer: this felt within reach in high school once I ranked top 200 North America in League of Legends (out of 100M+ players globally).
Despite this, I needed to support myself so I went to college and started learning to code. Coding came naturally (especially with 100 hour weeks) and I was soon skipping class to work at places like Hulu and Wieden+Kennedy (ad agency). Realizing that being paid to work full-time (vs. paying to go to school) sounded quite nice, I dropped out after 1 year to join Pinterest.
After Pinterest, I started a company called Skio which does subscription management software for brands on Shopify. In just 3 years, we've partnered with 1000+ brands (Liquid I.V., Milk Bar, Polaroid, Barstool, Unilever, KraveBeauty, Boba Tea Protein), reached $10M+ ARR (+profitable), and built an amazing team of 50.
With advancements in generative AI (video specifically), I saw an opportunity to help brands bring their stories to life exponentially faster and make marketing much better (hence Icon & building the first AI Admaker).
I love learning how we can help better. Feel free to reach out any time at kennan@icon.me.
Founders Fund

Founders Fund

Icon Investor
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Peter Thiel's Founders Fund is a venture capital firm. Its partners have founded and funded companies including PayPal, Palantir, SpaceX, Anduril, Flexport, Airbnb and Stripe.
Ron Shah

Ron Shah

Icon Investor
Ron Shah
Ron Shah
Ron Shah
CEO, Co-founder at Obvi, Co-host at Chew On This, Managing Partner at Gaas for SaaS.
Roman Khan

Roman Khan

Icon Investor
Roman Khan
Roman Khan
Roman Khan
Roman Khan
Roman Khan
President, Founder at Peak21, CMO at Raycon, CMO at Know Beauty, CMO, Co-founder at Linjer, CMO at Nutrition Kitchen.
Kennan Davison

Kennan Davison

CEO, Founder
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
CPO, Chairman, Founder at Skio (CEO 2021-2024, $10M+ ARR in 3 years, profitable).
Previously: Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends Challenger (Top 200 North America, 100M+ players globally), Y Combinator S20 (solo founder), Columbia (transfer, dropout).
Yunyu Lin

Yunyu Lin

Founding Board Member
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Head of AI at Ramp.
Previously: CEO, Co-founder at Cohere (AI CX / LLMs, acquired by Ramp), Nuro, Facebook, Y Combinator S20, Duke (dropout).
Kevin Jin

Kevin Jin

Engineering
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Previously: CTO at Kalder, Compound Labs, Robinhood, Rippling, Impira, Flexport, Google, Tesla, TSM, Vanderbilt.

Why us

Track record of things that can't be faked

Icon is the best team helping brands create winning ads in minutes.

Our CEO/Founder (who is writing this, sorry for writing in 3rd person) brings experience from Skio, Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends (Top 200 North America, 100M+ players globally), & Y Combinator S20 (solo founder).

At Skio (subscription management software for brands on Shopify), he was CEO/Founder of the company from 2021 to 2024 helping grow revenue from $0 to $10M+ ARR in 3 years (w/ 90% margins) and a team of 50 (on $8.4M raised). Skio is profitable and still growing >100% YoY.

Our tech investors include Peter Thiel's Founders Fund, Eric Nam (K-Pop), Alex Botez (Chess), Reilly Opelka (Tennis), Max Altman (Saga), Kevin Hartz (A*, Eventbrite), & execs of OpenAI, Ramp, Flexport, Cognition, & Pika.

Our D2C investors include Ron Shah & Ash Melvani (Obvi), Roman Khan, Nick Shackelford, Jimmy Kim (Sendlane), Kevin Lee (Immi), Justin Mares (Kettle & Fire), Steph Liu (Levitate), Jason Wong, as well as founders of Eight Sleep, Yotpo, Siena AI, Replo, Novel, Parker, GR0, DCL Logistics, Aftersell, Platter, Openborder, Prescient AI, Daasity, & more.

Our team has also worked with 1000+ brands like Liquid I.V., Milk Bar, Polaroid, Barstool, Unilever, Bulletproof, 100 Thieves, Vega, KOS, KITSCH, True Botanicals, mindbodygreen, Transparent Labs, GHOST, Wild One, OpenStore, The Nue Co., Immi, DRMTLGY, Boba Tea Protein, KraveBeauty, Glamnetic, Doe Lashes, Magic Mind, Remedy Organics, & Siete Foods.

Focused on building the AI Admaker

Icon is focused on building the AI Admaker vs. also juggling the underlying AI tech.

We believe our approach is fundamentally better because we're free to choose the best technology partner for a specific job.

To illustrate this, maybe one AI-video partner specializes in face closeups while another partner specializes in body movements (where face doesn't matter as much).

If we built all underlying technology in-house, it would create a fundamental conflict of interest where we can't offer a competitor's tool (that might be better) without losing revenue.

Products
Icon

Others

Admaker
(replaces CapCut, Adobe Premiere)
Create winning ads in minutes.
Replaces CapCut ($7.99/month), Adobe Premiere ($54.99/month)
check
x
Adspy
(replaces Foreplay, AdSpy)
Save time with AI-powered ad cloning.
Replaces Foreplay ($49-$99/month + $20/user), AdSpy ($149/month)
check
x
Ads Manager
(replaces Meta & TikTok Ad Managers)
Save time with ad manager auto-upload.
Replaces Meta & TikTok Ad Managers (direct use)
check
x
Creative Library
(replaces Recharm, Air)
Save time by storing, tagging, creating, & splitting videos with AI.
Replaces Recharm ($500-3K/month), Air ($250-$2K/month)
check
x
Creative Analytics
(replaces Motion)
Save money with built-in creative analytics.
Replaces Motion ($1K-$10K/month)
check
x
UGC Creators
(replaces Billo)
Save time & money with AI-generated UGC.
Replaces Billo ($99/video)
check
x

Ready to create winning ads in minutes?