⚡️ Today’s level up ⚡️
It’s the second week of January, and now it’s time to get a glimpse of what’s possible in your craft as a strategic seller. Today’s system is about unpacking what consistent 7 figure dealmaking looks like – and at a company that’s not Salesforce, Oracle, SAP, or some other behemoth.
Read time: <7 minutes
The path from $0 – $98M ARR (+ an IPO)
Let me introduce you to Juan George.
Juan is a friend of mine and we ran closely in the same circles when I was in the restaurant technology space from 2014 – 2017.
Juan was recently on The Pavilion Podcast, and he gave a masterclass in running an effective vertical-specific enterprise SaaS sales strategy.
I want to share it, because you’ll benefit from his story.
Let’s dive in…
Olo, Juan’s former employer, is the leading on-demand commerce platform for enterprise restaurant brands (I tried to get a job there in 2015, but apparently Juan was already doing so well, they didn’t need to hire me).
Olo is on the NYSE (symbol: OLO), and according to LinkedIn, they have 849 employees.
Here’s a quick snapshot of his journey:
>> Joined the company in 2007 during his 2nd semester as a senior in college
>> Had an amazing 15+ year run at the company
>> Recently exited from Olo after their IPO in 2021
>> Experienced the full startup dream over 3 key chapters
CHAPTER 1: Chasing Market Fit (7 years)
Juan started as an intern and dedicated himself to becoming a “student of the game.”
He learned from great mentors like, founder and CEO, Noah Glass.
Starting out, his role was mostly in Customer Success, dabbled a bit in Sales, and did end-to-end Customer Lifecycle work – which would later serve him well.
Like all of us in the beginning, he was just trying to figure it all out – while the company tried to find a market fit.
During this time, the company faced a lot of challenges and they could have called it quits many times.
Olo eventually found their fit and transitioned from a B2C company to a B2B2C company winning their first enterprise restaurant logo – Five Guys.
When Marty Hahnfeld arrived at Olo in August 2013 to run Sales, Marketing, and Success teams, “things started to click” for Juan and he left the world of Customer Success to pursue Enterprise Sales full-time.
Good move? Let’s find out…
CHAPTER 2: $2M ARR to $45M ARR (6 years)
Juan graduated to become a Sales Director, which was an Individual Contributor role.
The way Olo was structured was to have a Sales Director manage a large territory – one on the East Coast, one Central, and one West Coast (he was West Coast, being based in San Diego).
Juan spent 1,000s of airline miles visiting 100s of restaurant brand HQs.
He was the top Individual Performer at Olo during this high growth period closing deals with Wingstop, DineEquity, Jimmy John’s, Panda Express, Texas Roadhouse, Shake Shack, Cheesecake Factory, and many more.
At a macro level, Olo was the fastest-growing and top-performing enterprise software platform in the restaurant technology segment during this period. It would be fair to say that he was also the top individual performer within the restaurant technology segment during this time.
CHAPTER 3: $45M – $98M ARR, leadership, and going public (2.5 years)
During this phase, Juan transitioned to a player-coach role (VP, Enterprise Sales), leading the Enterprise team during the greatest year (2020) in the company’s history and witnessing the company go public on the NYSE.
2020: As an individual, he delivered 1/3 of the annual Enterprise location count through major wins across 10 deals. As a team, they delivered over 14k locations and $80M+ in TCV – the most impactful year in the company’s history in hist first year as a leader.
2021: After a record-breaking 2020, Olo went public on the NYSE in March 2021. They expanded the team to deliberately go after Large Enterprise and Convenience Stores, while continuing to deliver banner wins for the company.
During this period, Olo took 70% of the enterprise restaurant market, and more proudly, carried a 99% retention rate with their customers.
NEXT PHASE: Time freedom
Instead of jumping into a VP of Sales role at a startup (where average tenure is <2 years), Juan now has control over how he spends his time and who we gets to work with (hello “Intentional Income”).
He’s operating as a fractional sales leader with perfect-fit SaaS startups who aspire to do what Olo has done.
This is a prime example of where SaaS sales can ultimately land you with the right effort, strategy, and when good factors come together.
Now, let’s unpack Juan and Olo’s blueprint, and the lessons you can take into your own strategic sales strategy.
LESSON 1: Focus on one vertical
The company was born in 2005 with the vision that consumers would use their phones as remote controls for the world.
That could have led them down many paths, but after finding market fit, they decided to focus their full attention on becoming the gold standard for online commerce for the restaurant industry.
That maniacal focus paid off for both Olo and Juan.
LESSON 2: Be enterprise-first
When I was selling in the restaurant tech space, I was on a small enterprise team for a product that focused on SMBs but was trying to scale up to the enterprise space.
This is a mistake I see from a lot of late stage startups (and sellers who try to sell into the enterprise space).
Olo instead, focused on enterprise brands first. Building there makes it easy to trickle down to to the SMB market, should the company want to.
They were the envy of the restaurant tech space, and once I joined a company like this in 2018 (LivePerson), my selling opportunity was immensely amplified.
LESSON 3: Run a top-down play
Olo did an effective job establishing strong relationships at the Private Equity level (a lot of restaurant brands are owned by PE firms).
Educating these influential leaders about the emerging trends of commerce (and the efficiencies of an intelligent commerce tech stack) was a productive way to scale their impact, as many PE firms own several restaurant brands.
This established credibility and spurred introductions directly with CEOs of their portfolio companies.
LESSON 4: Run a top-down play
During all 3 chapters, Olo stayed lean.
Because they knew their Ideal Customer Profile (the enterprise restaurant brand), they could do more with less.
It became about hiring smart, capable people who can be experts in this category and run a large geography focused on long sales cycles.
This is the return to rigor all SaaS companies are trying to find right now.
LESSON 5: Scale w/ emerging brands
Companies, leaders, and individual contributors all want to work with the “cool kids on the block.” These are the high-growth, future enterprise brands of tomorrow.
By being the gold standard, you can take on a more advisory type of position with these brands and build long-term stickiness as they grow, helping you grow.
Plus, it’s fun to work with cutting-edge brands, people, and company cultures.
Like this? A free gift for you
I’m excited to share more stories and systems like this from active sellers from the Make More Hustle Less Club.
There are two core paths we’re focused on this year:
- 1. Become a Category of One Seller – How do you design a buying experience that makes it feel like only you in the world are capable of delivering the best results for your prospects and clients
- 2. Turn Intentions Into Income – Design purposeful work to deliver predictable profits – whether that’s as an active seller or working on building your own thing
If you are not already a part of this club, I want to provide you with our last session (80 minutes total) here for free to give you a sneak peek.
One member said “This is like getting a $1,000 seminar for $30!”
Check it out:
There are two ways to become a member based on your current status here.
See you inside!
When you’re ready, here are 3 ways I can help you:
This combines the 7 Steps to 7 Figures system along with an annual membership to our Make More Hustle Less Club where we put the system in action as a community.
You can book a 60 minute session with me here (however you save more if you do option 1 and bundle in a strategy call)
All Q1 slots are filled, but I will be selecting Q2 spots in about 7 weeks.