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Eric Keiles - Chief Entrepreneur In ResidenceThu, Jun 3, 2021 11 min read

How Backpacking Improved Our Sales Process

Strong Sales Execution Shares Similarities With Hiking

At age 55, it’s getting harder to hump up and down the mountains of the Appalachian Trail. So I decided to pursue what I call “flat walking.” I pick a rails-to-trail or tow path along an old canal and just start walking. I’ve lost 43 pounds with a combination of sensible eating and long-distance hiking.

On a good day, I can walk 15 to 20 miles. At an average speed of about three miles per hour, that can be the better part of the day just walking, and you can do a lot of thinking over five or six hours of hiking.

Lately, I’ve been thinking about sales process, sales enablement and sales strategy on those weekend walks. Mostly because during the work week, I’m chatting with prospects and clients about these issues. A lot of the conversations center around the changes occurring in selling due to COVID and what they might do to adjust.

On a recent Saturday walk through the Delaware Canal State Park, I started thinking about how backpacking is a lot like a sales process, and I’d like to share some similarities.

Start With Strategy And Planning

First off, you don’t just wake up and start walking. There are several steps to a long-distance hike, just like in sales there is no way to just start selling. The initial step should always be strategy and planning.

I start thinking about a hike about a week in advance. Questions arise like:

  • Where will I go?
  • How will I get there and back?
  • What will the weather be like?
  • What will lunch be?
If I didn’t stop and consider these issues before embarking on the day, it could lead to a really bad walk where I am unprepared, have bad timing and don’t reach my goal of finishing the hike.

In sales as well, we need to plan. We need a sales strategy that is carefully mapped out and considers all of the dimensions of an effective sales process. A sales process is a set of repeatable steps that a salesperson executes to take a prospective buyer from the early stage of Pre-Awareness to a closed sale.

Salespeople don’t like following imposed routines, and who can blame them? But did you know that about two-thirds of all salespeople don’t follow a sales process? It makes sense that sales reps who use a defined sales process outperform those who don’t. But how do you create a sales process for your organization that your folks will use? You make it easy.

Typically, a sales process consists of five to seven basic steps, including prospecting, preparation, approach, presentation, handling objections, closing and follow-up. While every company is different, you should create a process and encourage your sales team to join in on the creation of that process, understanding that every stakeholder will get better results if you plan in advance.


Get The Right Support

I have a great support team for my hikes. Actually, it’s just one person: my lovely wife, Bonnie. She blocks out the calendar for me, prepares a healthy and ample lunch, washes my muddy gear from the previous hike and checks the weather.

Salespeople need support for their endeavors, too. They need the marketing team to work with them to prepare the sales gear. This includes content to support the process, carefully crafted follow-up emails and sales sequences, technical experts from other parts of the company to join tricky conversations with prospects and of course killer presentations and simple agreements. Sales enablement is the process of providing the sales organization with the information, content and tools that help salespeople sell more effectively.

On the topic of tools, I’m a real gear guy. I want to have the best (and the lightest) tools to help me on my hike. This means having a sturdy backpack, walking poles, insulated water bottles, the most comfortable boots I can find, layers of clothing for any weather condition and a great hat.

Salespeople need tools, too. Too many companies do not put a lot of stock in the technology component, which is a must-have in today’s selling environment. I still see companies using spreadsheets to keep track of opportunities.

If you get anything from this blog post, please know that a powerful CRM can be the difference between success and failure for your sales efforts. Here are 10 benefits of investing in a CRM like HubSpot or Salesforce:

  1. Improved target prospect segmentation
  2. Better prospect experience
  3. Increased sales results
  4. Enhanced customer retention
  5. Insightful analytics
  6. Accurate sales forecasting
  7. Higher salesperson productivity
  8. Centralized database of information
  9. Powerful communications with prospects
  10. Automated reports

10 Little-Known Secret Metrics To Help You Improve Close Rates and Shorten Your Sales Cycle

Use Data To Your Advantage

OK, now we have our plan for the hike, we have support and we have the right gear. But what happens if something changes in our plan? An unexpected rain storm? The path is closed? Bears are sighted?

In sales, we must accept that the process is never linear. There is feedback and subsequent adjustments that have to be made. If you are not collecting data, start today. If your team is already collecting sales data, are you really getting the best use out of it? Is your data working for you? Is it improving your sales efforts and helping you make strategic decisions?

One study found that 43% of companies gain little benefit from their data, while 23% gain nothing from their data at all. The objective here is to collect good data, gain insight through analytics and use those learnings to make positive changes for your sales process.

Here’s an example of how data analysis can make great improvements. Our client created data centers – those back rooms that house the computers that run a business. They sold racks, wires, air conditioning units, lighting, humidity meters and everything else a company would need to protect and operate their servers and related gear. Their close rate hovered consistently at about 20%.

In their facility, they built a Disney-esque sample data center that prospective clients can visit to see and feel what their data center could be. Using sales data analytics, we uncovered that 89% of prospects who visited the sample data center bought something, but only 25% of prospects took the effort to visit the facility and explore the model data center.

Understanding that, we guided our client to build in to their sales process a visit to the data center. For those not local, they offered to fly them in and pay for the expense of the visit. Since their average engagement size was north of $300,000, this was a no-brainer. The sales close rate jumped to approximately 50% in less than four months simply by leveraging insights from the data.

Be Comfortable Saying ‘No’ When Needed

I want to touch upon one other reason that sales processes break down, and it’s about qualification.

I see too many salespeople actively pursuing leads that have no realistic chance of closing. They are working too many opportunities and don’t take the time to say “no” to the unqualified prospects. If they did, they would have more time to go deeper in conversation with the ones that are fit to close.

On my first trip to the Appalachian Trail, I was green. I was worried about not having enough gear, food and water to make it through the five days and four nights. I packed everything into my bulging backpack and set out with two buddies. By 3 p.m. on the first day, I was exhausted from carrying 55 pounds on my back. I learned on subsequent trips that I could have a great experience with just 35 pounds of supplies. What a revelation!

If salespeople would simply empty the unqualified rocks they collect along the trail in their backpacks, they could be more successful. It took me several years to have the understanding (and confidence) to say “no” more frequently than “yes.” But our close rate has never been higher with the opportunities we go after.

Stay Determined

You know what the last similarity is between hiking and sales? It’s what the sales guru Chet Holmes called “pig-headed determination.” If you want to get back to your car at the end of the hike, you’d better keep putting one foot in front of the other.

Similarly, if you want to hit the annual revenue target, you need to keep driving the team forward. With determination, I can hike longer and longer. And your sales and marketing teams can keep creating stretch revenue targets and hitting them, too.

I hope I got you thinking differently about your sales efforts. Ping me if you want to talk about your process or join me one Saturday on the trail.


Eric Keiles - Chief Entrepreneur In Residence

Eric Keiles is the co-founder and Chief Marketing Officer of Square 2. He is a leading sales and marketing strategist focused on pioneering a new marketing methodology. Along with his business partner Mike Lieberman, he is leading the revolution in how entrepreneurs change the way they think about marketing their companies. A natural entrepreneur himself, Eric has founded and grown five companies since 1997.