The Art of Enterprise Gifting With Justin Gilchrist
Justin Gilchrist, founder of Wellbox, is our guest in this edition of our Founder Spotlight Series.
Justin has been an entrepreneur for over two decades, exiting a technical due diligence firm in 2016 and running a major corporate hospitality business in Greater Manchester. When the pandemic hit and corporate catering ground to a halt, Justin scrambled through several business ideas before founding Wellbox—a hybrid e-commerce and software platform for enterprise gifting that reached seven figures in revenue within its first two months.
I sat down with him for the podcast to talk about how a crisis forced a new business model, why he chose bootstrapping over venture capital, and how Wellbox integrates agentic AI workflows to scale operations. His answers are lightly edited for length and clarity.
The conversation
Could you tell us a little bit more about you and about the work you do?
I've been an entrepreneur for as long as I can remember. I've got a background in mostly technical companies. Prior to doing what I'm doing now, I had a company that handled technical due diligence for people acquiring internet companies, generally between $2 million and $10 million—doing the work neither an accountant nor a lawyer could handle. We were acquired in 2016.
I then tried a few things that didn't work, which seems to be an ongoing theme of my life: trying things that don't work to eventually stumble on the thing that does.
I also own a corporate hospitality company, South, which I've had for 21 years. We're one of the largest privately held corporate catering companies operating across Greater Manchester. During the pandemic, corporate catering went totally flat, and we had to scramble desperately at other business models that might work for us. That is eventually how we stumbled upon Wellbox, which is the company I run and operate today, where I lead growth.
Was Wellbox around before or after the pandemic?
There was no Wellbox before the pandemic. Offices closed everywhere, so with no one in offices, there was no need for catering. We weren't B2C or hospitality enough to get walk-in traffic or grants. We had around £50,000 to £60,000 a month in costs going out, so it was a really stressful time.
It was a case of going back to where I started—just trying things out. We tried a food delivery startup for people who wanted lunch at home, and chilled meal delivery for other companies. But with £50k to £60k of monthly expenses, whatever we did had a high bar to meet within a two- to three-month period.
The last of our desperate ideas was delivering snacks to corporate companies wanting to send something physical to staff they had furloughed or who were working at home. Wellbox was the only idea that hit in a significant way.
Today, we're a hybrid between e-commerce and software. We operate a software platform that lets companies store their data securely within the UK, and we handle the physical distribution and warehousing of those gifts as well.
How did the name Wellbox come about?
I'm historically terrible at names and a firm believer that when you start something, you should spend the minimal amount of time on things that don't give you validation to begin with. For me, if I couldn't make sales happen within three to four days, we couldn't move forward.
The name came from sending a WhatsApp to eight or nine people I know to crowdsource ideas and see what domains were available. The name was average at best, but it gave us a way to get out real quick with something that said what we did and was easy enough to trademark.
For the first two years, we actually just used the logo from our corporate catering company, swapped the word "South" to "Wellbox," and kept the colors because it was the quickest way to validate the idea. We rebranded a year or two in.
How would you describe the experience and the reception? How has it been?
It’s been amazing. We saw crazy growth within the first year—within two months, we’d already hit seven figures in revenue.
It was pandemic luck. A lot of companies thought that pandemic hype would stay, but we were realistic enough to know we had to make hay while the sun shone because at some point things would return to normal and spending would dip, which it did in 2023. Fortunately, we had the foresight to lay the foundations for the long-term business we have today, which appeals to current behaviors rather than just playing on pandemic trends.
What kind of companies do you tend to work with? Are these physical companies or are they online-based?
Off inbound alone—we have no sales team—just over 87% of the FTSE 250 are our clients or have purchased from us. That includes major banks, insurance companies, large tech firms from Google to TikTok, car manufacturers, energy companies, and retailers like Harrods.
They tend to center around enterprise-sized companies with a lot of employees. They use us split between employee gifting—which is why Christmas is our busiest time of year—and sales/marketing teams using us for prospecting, client retention, and vendor thank-yous. We work with smaller companies as well, where we know we're genuinely making a difference to the people receiving the gifts.
How big is your team, or how big have you guys grown to now?
Our core team is around 11 people, spread across customer support, product development, design, and office management.
Because of the seasonal nature of gifting, we operate a lean core team and scale up temporary labor in warehousing and operations during our peak times of year.
When you work with clients now, do they have an idea of what they want or do you work with them to come up with their own gift?
We sit towards the middle of the market. We don't go after clients who need super bespoke, boutique agency design, but we frequently help clients put together gifts for campaigns once we know their objective and budget.
For example, clients doing outbound sales who struggle to convert middle-of-funnel leads will send a small gift. We work with them to figure out the cost for that send-out and monitor the ROI based on that conversion.
How do you source your vendors?
We have someone full-time whose job is dedicated to sourcing and purchasing. As a B Corp, supply chain scrutiny is important.
We try to work with smaller, independent UK entrepreneurs, particularly minority and female founders. We buy in big volumes upfront, which gives them liquidity and gives us economies of scale to pass on to our clients. A lot of sourcing comes from word-of-mouth or seeing a new brand on social media that has great ethics and practices.
When a client uses you guys, what does the end product look like? Is it branded in the client's box, or how does that work?
It depends on the client and the context of the gift. We do a lot of bespoke and branded packaging—printed locally in Manchester using sustainable items and eco UV inks—for things like new starter packs, where you want a new hire to feel connected before their first day.
However, if you're sending a client or customer a thank-you gift, branding every item can send the wrong message; it can look like a marketing exercise rather than a sincere attempt to say thank you. In those cases, clients go with our non-branded Wellbox gifts.
How do you use data in your business?
Data is really important. Having done data analysis before AI, it’s about understanding what story you want to tell.
We look at web analytics to see which products people linger on, what gets added to our bespoke gift builder, and where questions get generated. We use that to inform what new gifts or suppliers we look for next. We also analyze feature usage inside our app to decide what software features to build next.
Enterprise gifting is complex because a buyer might be responsible for gifting anywhere from 20 to 15,000 people on a £50 tax-free budget per person, all with different dietary requirements or lifestyle choices. Data and software allow us to give recipients choices or swap options to keep everyone happy.
Who is your champion in these companies—is it HR or sales and marketing?
Our ideal customer profile is split roughly 60/40 between HR and sales/marketing.
HR handles milestone gifting—anniversaries, new babies, weddings, or bereavements. They tend to use softer, more emotive language focused on how a gift makes people feel.
Sales and marketing teams use gifting for prospecting to cut through noisy email inboxes. They are focused purely on ROI and hard conversion numbers. We've had to build distinct messaging systems to speak effectively to both.
What would you say has been your biggest challenge to date?
Historically, I would have said staff. But over the last five years, we've had the exact same core team, just adding people to it. The team here is amazing.
The biggest challenge has been growth and scaling post-pandemic. We grew so fast during the pandemic that there was a question of whether we raise VC money and scale rapidly or stay bootstrapped and figure out our identity outside the crisis. Resisting the temptation to take VC money was hard, especially watching competitors scale fast with investor capital.
Now, seeing many of those VC-backed companies struggle with massive overheads when revenue dropped, I'm glad we stayed bootstrapped. We've been profitable for a while, which allows us to experiment without board pressure and keep a tight-knit core team DNA.
What would you say has been a moment or a win that has really been like, "Yes, I've got this"?
The biggest win is definitely the team—I feel like I've 80% lucked out and 20% learned from 25 years of making every hiring mistake under the sun.
The second biggest win is our resilience. More than 67% of the gifting companies that boomed around the pandemic no longer exist. Between 2023 and 2024, the UK economy went through a flat period with supply chain disruptions, changing budgets, and economic uncertainty. Navigating that and staying profitable has been a huge achievement.
How does AI fit into your company, and how do you guys use it?
We use AI deeply because of our technical background.
We’ve built agentic workflows inside our software. For instance, setting up a new multi-brand gift product used to require taking photos, collecting attributes, writing descriptions, and updating Google Merchant Center—a process that took roughly four hours per product. We built an internal agentic workflow that cut that down to 10 minutes.
We also use OpenAI to generate scripts for Illustrator to produce vector-based packaging designs automatically. On the client side, AI helps users search for gifts via natural language prompts and automatically builds customized gifting portals.
If businesses actually pushed the boundaries of current AI models rather than waiting for the next hype cycle, they’d be surprised by how much operational friction they could eliminate.
How do you use LinkedIn, and what would you say has been your most effective strategy?
Badly! I ignored LinkedIn for most of my career because I never had a traditional job. I only started posting four months ago.
I’m realizing that organic search and paid channels are eroding, and attention is everything. Building a personal presence and sharing authentic, real-world operational stories is critical now because AI-generated noise is everywhere, but real battlefield experiences still resonate.
What's one key takeaway you would like readers to take away from this episode?
If you're anywhere near the start of your journey, just start. Don't obsess over things being perfect or even right. You've got plenty of time to correct it along the way, but get to whatever validation looks like for you as quickly as possible before you lose momentum.
Closing thoughts
Justin’s journey with Wellbox highlights how constraint and crisis can spark long-term enterprise innovation when paired with rapid validation and operational discipline. Here are key takeaways for founders:
Move fast to validate: Focus initial energy on getting sales and proof-of-concept rather than perfecting branding or names.
Bootstrapping offers control and resilience: Profitability and lean teams provide the flexibility to navigate economic downturns without board pressure.
Automate the repetitive: Use AI and agentic workflows internally to reduce manual tasks from hours to minutes.
Match the gift to the context: Understand the psychology of the recipient—differentiate between branded company swag and genuine thank-you gestures.
Want more conversations with founders?
Follow Justin Gilchrist on LinkedIn and learn more at wellbox.co.uk
