7 Mins Read

How I Made $400K Selling Burritos in 7 Months

Brandon Fluharty |

Brandon Fluharty |


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⚡️ Today’s level up ⚡️

Today’s edition breaks down how we systematically won a multi-million dollar deal with Chipotle – one of my favorite career wins.

Let’s go!

Read time: <7 minutes


It started with the Diamond Standard

Most AEs I meet don’t spend enough time with their SDRs, truly working through how to be more strategic with their outreach…and it’s costing them hundreds of thousands of dollars in lost commissions.

When I was at LivePerson, I was fortunate to work with some amazing SDRs. One of the best was Grant Horvath, who is now an Enterprise AE.

Grant was always trying to make my job easier, which I greatly appreciated, but he also wanted to deliver a higher standard to the prospects on our strategic account list, which I appreciated even more.

It’s critically important, because the tone with a strategic account is set early in those first conversations.

Grant was a master at setting a high standard early on before passing it over to me.

We’d often go through extensive exercises of being the customers of our prospects (the huge benefit of being a B2B2C seller) so that we could develop a distinct point of view and key insights that would inform our position with that account – something I call the Diamond Standard.

Grant was able to connect with one of their VPs on her mobile as she was getting in her car to work. She agreed to a discovery call and ended up becoming a true Mobilizer for the deal (and absolute dream to work with).


Key ingredients that progressed the deal

After one discovery call with the VP and an additional one with one of her direct reports, I was on a plane to their gorgeous office in Newport Beach, CA.

In that initial POV meeting, we had two hours with their team, and I had two technical resources with me and a business executive – our head of Gainshare to match their team of 8 on their side from various departments.

It’s important to note, Chipotle was high on my list, not just because it’s one of the most recognized Fast Casual brands out there, but because I had experience selling enterprise restaurant technology in my previous role.

Because of that, I knew QSR brands operate lean at the executive level and are accustomed to moving fast with big decisions – one of my key criteria when I did my Diamond Account filtering.

This helps encourage success through design before I’ve even connected with the brand.

Without getting into too many proprietary details of the engagement, here’s a list of the core ingredients that helped progress the deal:

1. We got into a design session early in the engagement (in-person meeting number 2)

As experts in their space – digital ordering, restaurant design, and quality ingredients, we knew they had a distinct point of view on the restaurant experience of the future.

As leaders and experts in our space – conversational design, conversational commerce, and digitizing customer care, we too had a distinct point of view on the restaurant experience of the future.

We used a design session to identify where those two perspectives intersected.

Tip: Host the design session offsite (but close to their office) to eliminate distractions and set up a circle to encourage collaboration (vs classroom style). Our session ran for about 4 hours.

2. We zoomed out before zooming in

By using the design session to find where our perspectives intersected, we could think openly and uninhibitedly on innovative use cases to pursue.

That gave us the ability to ideate on conversational commerce, conversational customer support, conversational marketing, and the conversational workforce.

By zooming out, we broadened the scope of our opportunity and brought to life a full company wide transformation (with their help!). All we had to do was guide the conversation.

We ended up identifying the two areas that made the most sense to pursue out of the gates, which were conversational commerce and support.

By the way, my first call was in October, the first meeting in December, and the design session was in January and we had enough to start building a thoughtful business case in that time – the beauty of applying design thinking in sales.

3. We invited them into our customers’ world early

The next step was to ensure we were a cultural fit for one another.

That meant playing a bit with them on our turf, so I invited them to one of our customer events in Dallas in February where they had a chance to hear directly from other major brands who were 12 – 18 months ahead of them on their Conversational AI transformation journey.

LivePerson is known for their marquee executive events, so you better be sure I was going to leverage that experience to wow them (it helped – a lot!).

4. We taught them how to buy a Conversational AI transformation

At every engagement, I would always end with a visual of where we stood in the transformation process.

Yes, it had components of the buying steps, but it also went a level deeper and identified steps to ready themselves to become a fully conversational brand, things like how to rethink new roles in the contact center, how to set up their systems to succeed early, risks to avoid, etc.

Because I wasn’t just fixated on the buying steps, it elevated the experience to feel more real – a project that they needed to think deeply through. They really appreciated that.

5. We thought and acted big, and assembled the right team to match

My early discovery calls were centered around basic things – they were doing initial research for chatbots for their customer care use case.

Had I kept the conversation there, it would’ve been easy to be put in a small box and only solving a $250K problem. But I knew we could solve a $25M challenge and talk about a $50M opportunity.

To do that, I kept the account team small, but capable. I not only recruited experienced people on our side that had the chops to pull off a large transformative deal, but those who I knew would be excited to pursue changing an iconic brand in the restaurant space.

Remember, the internal sell can be just as important as the external one. Be sure to excite and recruit internal stakeholders that you know will add value and be a great cultural fit for the prospect or client.


The winning touch

When it came to drafting our proposal (which had to be directed to the CEO because of the deal size), we built it asynchronously with our Mobilizer.

We literally drafted the Google Slides together. That guaranteed that the flow, images, and structure looked like an internal business case and not a sales proposal from a new vendor.

The outcome: We closed an 8 figure deal that included an immediate $2M booking and we earned $1 per transaction through the conversational ordering experience once deployed.

I’ll take that all day…and with a side of guac! 🥑

The main lesson: You need to collaborate for success.

You can’t win massive deals alone.

That’s a wrap. See you next week!

By the way, I’ll be talking with James Buckley on May 16th of the Sell Better podcast breaking this deal down in further detail. Click to reserve your spot:


When you’re ready, here are 3 ways I can help you:

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2 | Book a 1:1 coaching session right now

You can book a 60 minute strategy session with me (although the Pro option in the 7 Figure Seller OS above provides access to 1:1 coaching with me at a 70% discount – just 12% of available slots remain for 2023).

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For any sales leaders or brands, to keep Be Focused. Live Great. free for the community of 10K+ enterprise and strategic sellers, I am offering sponsorship space for this weekly newsletter. If you’re interested, email: hello@befocusedlivegreat.com

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