The last 12 months have been my own real-life version of “Undercover Boss,” transitioning from being a CEO to a sales rep back to a CEO. This is my journey over that time and the valuable lessons I learned along the way.
I thought I understood what it took to be a successful sales executive. I was wrong.
Ask anyone who has worked with me, and he or she would tell you that I am a hands-on CEO. I am heavily involved with employees and customers (to the extent my team lets me). In fact, I often help reps gain access and land meetings with senior-level executives in their accounts by sending prospecting emails. I am not afraid to roll up my sleeves and get dirty.
Because of that involvement, I thought I understood what it takes to be a successful sales executive in today’s world — but I couldn’t have been more wrong!
I am certainly not alone in this area. You don’t need to look any further than social media to see self-proclaimed sales gurus, who are not selling every day, spewing the latest “research” based self-reported survey data (usually bull).
After working in the sales and marketing space for the last 30+ years, in multiple roles from sales rep to CEO, I found myself back in the field and on the front line, selling enterprise, cloud-based technology. I have failed a lot in my career and have had my share of successful runs too, but I was now back at ground zero.
How did I arrive here? A conversation with a friend (see No. 5 below) turned into an offer to help his company with its go-to-market. This offer led to an advisory role and a personal investment in the company. Here is what I learned over the next nine months as “president” (which really was just a fancy title for the company’s only sales rep). It started with a big slice of humble pie and turned into eight valuable lessons for success in sales today:
1. Believe in What You Do
Its impossible to expend massive effort over the long haul — while experiencing failure, rejection and dejection every day — unless you believe, with all your heart, that you are making an impact. Your mantra must be that if people are not buying from you, you are doing them a disservice, because your solution can impact lives. This point is non-negotiable. Don’t start unless you care.
2. It Takes Massive Effort to Build Your Pipeline From $0
No really, I mean a massive effort — effort that is sustained every day, for months. You cannot miss days, fake it, shortcut it or “hack” your way to it. Research, network, connect, email, text, call and use social media to create a massive sustained effort for at least nine months, no matter how many deals you are working. Don’t take your foot off the accelerator, no matter how successful you are. Buckle up for a brutal and long ride if you want to succeed. (And, as noted, this ride doesn’t happen without a belief in where you are going).
3. Failure and Rejection Are Part of the Game Every Day
And I mean every day. You will feel dejected, but this is a natural human emotion. Pick yourself up, come back tomorrow and do it all over again (see No. 1). Some days, it’s hard. Work for that one small win each day, and don’t stop until you achieve it. I suggest a three-minute cold shower each morning to prepare your mind and body for intentional discomfort.
4. Execute on the Basics
It had been over 20 years since I’d been in a direct sales role, but the basics still applied. Forget the latest technology or nifty hacks; sales is about people talking to people. Keep it simple; do the research, engage with social media, send messages, text, make calls, follow up — and then do it again and again and again (to the same people). You’d be surprised how many of the people you are competing with don’t have the stamina for these basics.
5. Relationships Matter
I was lucky; over the years, I had invested heavily in my network. Now, I was able to make some withdrawals and ask for help. Most came through with flying colors. Build a solid network — not just of followers but of people you engage with. Your network doesn’t have to be large (although it helps). Always look to help others through thoughtful engagement. It is better to engage thoughtfully with your network then to cast a wide net for your own benefit.
6. It’s Situational
Just like in sports, sales reps must adjust to the situation in front of us. We cannot blindly run a play or a strategy because it’s what worked before or it’s what we were trained on. Understand your “team” and your customer’s “team,” and adapt accordingly. No single strategy, methodology or message fits all situations. Learn to be agile and situationally fluent. Know when to be disruptive, when to be solution-focused, when to be value-focused and when to leverage your relationships.
Your ability to understand what you’re facing and adjust accordingly is the difference between success and failure. The best quarterbacks can recognize a situation and adjust their play, and the best salespeople are situational, adjusting their strategy based on the buyer’s journey. You will fail most of the time if you run the same play every time. Your ability to adapt will make you a differentiator.
7. There Are a Minimum of Four Buyers
In every deal I closed, there were between four and seven buyers. Don’t make the mistake of thinking that your deal is different because you have a strong relationship with your one or two sponsors or “coaches.” Even if you think you have spoken with all of the buyers, look for more. If you don’t, you will reach what you think is the end, only to have other influencers come out of nowhere, putting you back at square one. I made this mistake more than once.
8. Your Story Matters
Your story is the heart of everything you do. Without it (unless you have some killer technology that no one else has), you won’t close sales. Your story must also be adaptable for the situation you’re facing. Know your story, own it, and deliver it with passion and conviction. You will grow sick of it sometimes, so you’ll need stamina. Know your story cold; only then will you have the situational fluency of a world-class performer to adjust your story to your audience for greater impact.
Sales takes a unique individual — one with commitment to service, stamina, perseverance and the ability to execute on the basics every day. I am proud of the work we did and the impact we made while I was the “sales undercover boss.” We added some world-class customers and brought awareness to a company that had very little.
Never forget that selling is a team sport. The effort by the entire team helped secure Series A funding that will support continued momentum and growth while bringing on top talent to continue to scale and succeed.
I’m back in the CEO role at VantagePoint Performance now. While I’m still a hands-on CEO, I am better able to serve and engage with our sales team. What’s more, I have a new perspective — one that’s grounded in an understanding of the massive effort, complexity and difficulty of the field sales role. I am grateful for effort it takes to be a world-class sales executive.
Sending you much positive energy on your journey to success!