6 Mins Read

Designing A Better Buying Experience: The Home Field Advantage Playbook

Brandon Fluharty |

Brandon Fluharty |


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⚡️ Today’s level up ⚡️

Today’s edition focuses on a purposeful play you can use as an enterprise seller that leverages the strategic power of your company’s HQ.

Let’s go!

Read time: <7 minutes

If you missed last week, read it here.


Designing a better buying experience

Back in 2015, when working remotely as an Enterprise AE at a late-stage startup, I pushed my win rate up to 60% by doing one simple thing: I invited my prospects to a one to two-day evaluation session at our HQ in San Francisco.

At the time, I was selling an iPad and cloud-based point-of-sale solution. Then, moving to the cloud was a key initiative for many multi-location brands, and there was a lot of competition. Selling on features and price was not going to be enough.

So, I started designing a better buying experience for my prospects.

I realized that those I was competing with fell into two camps – large, stodgy incumbents who didn’t care about designing a good buying experience (they relied on their enterprise capabilities) or small upstarts who weren’t able to deliver a better buying experience (who relied on giving new customers whatever they wanted).

To break through the noise, I needed to create a memorable experience that served four key functions:

1. Qualify the prospect

2. Shorten the sales cycle

3. Build enterprise-level credibility

4. Amplify the cool factor of a startup

Let’s break down how it worked and why it was so effective.


Leveraging home-field advantage

Qualify the prospect

After completing initial discovery with the prospect, I would invite them out to San Francisco to conduct their due diligence.

At that time, regardless of where the client was located, it was not all that hard to sell a visit to San Francisco. For some, I was even able to work in a visit with our partner Apple at their HQ in Cupertino.

I’d normally have a Zoom conversation, then an in-person visit at their company, a few more conversations, and then if there was a legitimate path to secure their business, I would invite their key evaluation team to San Francisco as a final close.

If they were willing to invest a few days to spend quality time with us, I knew my chances of winning were high, and they were serious about working with us.

Shorten the sales cycle

By getting them on our home turf, and being very purposeful with what we would do during our time together (which I’ll share in more detail below), I was able to cut out an additional three, four, five meetings and unnecessary travel to their HQ.

That’s because, as a lean startup, we could accomplish more in a single visit where I could easily rally all of the key resources needed to make a compelling presentation for our visit – partners, sales engineering, security, support, client services, and our founders.

It was so thorough that the natural next step was to secure an order form.

Build enterprise-level credibility

Because it was risky for CIOs and COOs of multi-location restaurants to move to the cloud, I needed serious backup.

Being on their home turf with just me and a solutions engineer wouldn’t cut it.

When it came to talking about the robustness and security of our platform, I would take them down a couple of floors where our security and product team lived. I needed special clearance, so I had to have someone come out and meet us, which had a dramatically serious effect in and of itself.

Plus, when it came to answering highly technical questions, I had subject matter experts who could do a far better job than I could.

Amplify the cool factor of a startup

Let’s face it, when you’re flying in from Lebanon, TN or Oklahoma City, OK, and step into the buzz of a startup with hundreds of young professionals, it’s hard not to feel the energy.

The iPads on the wall, the kombucha on tap, the ping pong table, and the sweeping views of San Fran from the rooftop were all elements that left the prospects with a lasting memory.

I would always round out their visit with a drink together on the rooftop around sunset. We’d casually discuss their takeaways and what gaps needed to be tightened up. They always left a bit smarter and with big smiles on their faces.

The winning blueprint

This experience was not left to chance – because of a well-thought-out system, I could repeat and leave each prospect feeling like we were working just for them.

Here’s the agenda and the key details of this winning experience:

Own the itinerary. Before the visit, I would know exactly when they arrived and where they were staying, and I would craft a detailed itinerary from touchdown to departure.

+1 touch: Knowing one of our key competitors (but a smaller, less sexy company) was based in San Diego, I would always invite them to visit them first. Why? It showed confidence and built credibility, but it also drew a huge compare and contrast, leaving them with the type of lasting experience I knew would edge in our favor.

The agenda. It was about 80% business and 20% personal. If they were visiting just us in San Francisco, this would be the typical day:

– 8 AM – 9 AM: Breakfast and coffee across the street at a cafe (that also happened to be a client that used our POS so that they could see it in action).

– 9 AM – 9:30 AM: I would walk them up to our main floor, where I reserved our main conference room to walk them through the agenda and always had our founders come in to greet them casually. This set the tone and intentions for the day ahead.

– 9:30 AM – 11:30 AM: Custom demo. We would move to our design lab (training room), where we had mock setups for restaurants, retail, and grocery. I worked extensively the day before with our solution engineers, inputting and customizing their menu so we could showcase every one of our various products in action on both the front end and back end. I encouraged the prospect to try to “break our system.” They never could.

– 11:30 AM – 12:00 PM: Break.

– 12:00 PM – 2:00 PM: Lunch. I would order an Uber Black car, and we would travel to a busy, higher-end restaurant (also a client of ours) so they could see our platform in action in real life. I would always arrange for the owner to come by and speak with them and answer questions.

– 2:00 PM – 3:00 PM: Customer success. I would invite our head of customer success to walk them through our enterprise plan for support and implementation services.

– 3:00 PM – 3:30 PM: Break.

– 3:30 PM – 4:30 PM: Security review & product roadmap. We would travel two floors down and invite them to an open Q&A session on security and our future product roadmap. We would start training them on what our top customers think about from a risk perspective and how to take advantage of being a part of our Customer Advisory Board to influence the product with key enterprise features they wanted or needed.

– 4:30 PM – 5:00 PM: Executive alignment. This is when I would invite back the founders to share the story of the company and ensure that we were in full alignment as partners.

– 5:00 PM – 5:30 PM: Define next steps. I would close by walking them through pricing and our plan for procurement and implementation.

– 5:30 PM – 6:00 PM: Casual hangout. We’d grab some beers from the communal kitchen fridge and move up to the rooftop, where we’d typically be joined by the solution engineer, with whom they’d also come to develop a relationship over the course of the engagement.

I would always recommend a few great restaurants (of course, all clients of ours) to have dinner on their own or allow them to explore the city on their own.

+1 touch: Pay attention to the small details – from using their exact logo to display on the welcome screen when they arrive to encouraging long, healthy conversations with people in the org they jive with. The small details will add up to stack in your favor for a big win.

Helpful? If so, let me know.

See you next week!


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