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David Fletcher of ClearSale: “Establishing relationships and trust”

Establishing relationships and trust. It’s hard to establish relationships and trust with your staff without a consistent interaction with them. For example, I provide a weekly standing call with each of my sales and marketing team members to make sure we are up to date and I can provide some oversight into their actions. This […]

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Establishing relationships and trust. It’s hard to establish relationships and trust with your staff without a consistent interaction with them. For example, I provide a weekly standing call with each of my sales and marketing team members to make sure we are up to date and I can provide some oversight into their actions. This helps because it’s difficult for sales managers that have a remote sales team to believe they are always working.


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing David Fletcher.

David Fletcher serves as Senior Vice President of Sales at ClearSale, a card-not-present fraud prevention operation that helps retailers increase sales and eliminate chargebacks before they happen. As a serial entrepreneur, he understands the particular pain points that affect business owners today, and how fraud management can provide real-world solutions to those problems. At ClearSale, he spearheads business development, sales, partnerships and alliances with top e-commerce organizations.


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

After graduating from George Washington University with a degree in Business Administration with an emphasis in Management and Operations, I started my career in sales in the early 90’s where I was selling in a 100% commission position as a technical recruiter in the IT space. I later became the VP of Sales and Marketing for a large systems integrator in Washington, D.C.

After 2000, I branched out and started my own firm doing systems integration, which grew into more sales and more speaking engagements, guest appearances, and training for other companies. That’s how my sales brand was born.

Since then, I started three other companies (two survived, one didn’t) and then continued doing sales coaching and training which developed into a marketing agency, specializing in inbound marketing and HubSpot. After being a HubSpot consultant and working with the product development team over time, I wanted to get back into sales enablement. Therefore, I started another business where we focused completely on sales enablement as a HubSpot partner and ClearSale became one of our customers. I was their consultant and then transitioned into a sales leadership role.

As a serial entrepreneur, I understand the concerns of modern merchants navigating the development and management of an online storefront. In my role at ClearSale, I remain a driving force in sales, where I have the opportunity to apply years of experience and energy for marketing and sales behind a product and team that I believe in. Mentorship and coaching are key elements of my leadership style, combined with infectious energy and deep knowledge. In May 2019, I officially joined ClearSale. It’s been a little more than a year-and-a-half and I’ve enjoyed every minute of it.

Can you share the most interesting story that happened to you since you started your career?

One of my most interesting stories was when I was a VP of Sales for a Systems Integrator in Washington DC. We had heard of a potential SAP opportunity with a large manufacturer in New Jersey. After doing some research, I learned the CIO was an avid golfer so I looked for a local golf course near his office and invited him out to play a round of golf. Much to my surprise, he accepted. At the turn he finally asked me, “So what are you trying to sell me?” I quickly responded, “Not a thing. Just because I have sales in my title doesn’t mean I’m always selling. I want to build my network of IT Executives in the NJ/NY region and you made the list. There are plenty that didn’t.” He gave me a long stare followed by a nod.

We ended up playing another round of golf 2 weeks later and he asked me more about my company. As I was sharing our value proposition, I was getting plenty of head nods in a very positive manner. After my pitch on the 7th hole, he didn’t really say much. I wasn’t feeling very confident due to his silence. After a quick lunch and teeing off at the 10th hole, he said, “I might have an integration project that you can help me with.” My response, “Really? Tell me about it.”

We went on to play four or five more rounds of golf, had plenty of dinners and a few drinks. He signed a 3.1MM contract with my firm without him and I ever having a meeting in an office. We only met on golf courses and in restaurants. I share this story not only because it’s so interesting, but because it goes to shows that the relationships you create and the value you provide is what sells. It will do the selling for you at times.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Back when I was an executive recruiter placing IT professionals in the Baltimore metro market I had a very funny and embarrassing mistake. I was in the process of hiring another technical recruiter to join my team. I won’t tell you what company she was with, but you’ll figure it out shortly. I met with her two or three times and decided to make her an offer. It was an offer that was better than her current compensation plan and the opportunity seemed to be a better fit for her. She verbally accepted our offer and I quickly pulled HR in to send over her offer letter.

When she went into the boss’s office to resign, the owner happened to be there. She didn’t want to resign in front of the owner, but he picked up on the fact something was wrong and asked her to come in and speak freely even in his presence. So she did, and the owner was not happy! She was their top recruiter and he did not want to lose her. He was able to convince her to stay and then followed up with me to let me know. And let me know he did! He blasted me over the phone. My coworkers hear me say, “I don’t care who you are” a few times during the conversation and when I was able to get off the call, everyone in the office was asking me what happened. I told them and they were roaring with laughter, I didn’t get it? What was so funny about this owner letting me have it for recruiting one of his best performers? It turns out, that he was not just the business owner, but part owner of the Baltimore Ravens and best friends with my boss, the owner of my firm. Fortunately, when the dust settled everything was ok with all parties involved.

What advice would you give to other business leaders to help their employees to thrive and avoid burnout?

Focus on the mental and emotional well-being of your employees! You must get your employees to take time away from their home offices. Since COVID-19, most professionals are working from home and as a result, are working more hours than they ever have before. This can lead to burnout. You must be the leader that helps the staff focus on a positive work-life balance.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

I have been managing remote sales staff since 1999. My first remote employee was when I was the VP of Sales and Marketing for a Systems Integrator in Washington, DC.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

Five main challenges of managing a remote team include:

  1. Establishing relationships and trust. It’s hard to establish relationships and trust with your staff without a consistent interaction with them. For example, I provide a weekly standing call with each of my sales and marketing team members to make sure we are up to date and I can provide some oversight into their actions. This helps because it’s difficult for sales managers that have a remote sales team to believe they are always working.
  2. Communication. As I mentioned above, I hold standing 1:1 video calls each week with my staff. The one thing that I preach to my staff is to over-communicate. If you think you already told someone something about a customer, a deal, or a project, be sure to tell them again!
  3. Motivation. Motivating a remote sales team can be quite difficult at times. Setting goals and tracking accomplishments has helped me overcome this challenging task. Celebrating your wins is something many companies struggle to do. I also like to provide ongoing one on one coaching with the sales team. During this time, I am able to motivate them by providing feedback, strategy, assistance and anything else they might need. I have found this to be something the sales staff looks forward to each week
  4. No sense of Team. Team meetings is step 1. This meeting must be a regularly scheduled meeting for all team members to come together. Also, there should be some sort of chat technology in place that allows team members to communicate with one another almost as easy as they did when they were in the office together. There are great tools available such as slack or MS Teams to help accomplish this.
  5. Technology. If not handled correctly, technology can quickly become a barrier to success. We need quality technology to communicate with one another in a quick, precise, and efficient manner at any time during the day. This can only be done with the right technology in place.

Based on your experience, what can one do to address or redress each of those challenges?

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language, but not when someone is remote.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

The three most important pieces of sharing “constructive criticism” looks like this.

  1. Always do it over a video call so you can see the emotions of your remote employee.
  2. Always do it in a 1:1 situation, never during a group call.
  3. And most importantly, have empathy! Remember, this remote employee might be new to working from home, might have young children that are home-schooling, and might struggle to stay focused due to the dog barking, the neighbor cutting their grass, or the delivery that just came to the porch. Be mindful of how hard working from home can be for some.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

First and foremost, giving any constructive or negative feedback should never be done over email if possible. However, if you must do it over email there are two very important points to keep in mind as a leader.

First, start your email by showing appreciation. Appreciation for the project you are about to provide feedback on, or maybe it’s feedback for an email they sent to a customer with a late invoice. Whatever it might be, start by thanking them for the effort, recognizing the work they put forth before sharing the criticisms.

Secondly, provide the employee with some direction that will be very specific, actionable, and of course, positive. In other words, don’t focus on what they did wrong, focus on what they can do different to improve.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

OVER-COMMUNICATE! One of the biggest things a team that recently went remote will tell you is that they are struggling with communicating various topics amongst the team. When in the office, it’s easy to keep one another up to date. Sometimes, you just overhear the conversation and it provides the update that you need. However, when you are working from home, the only updates you get from your team are the ones they tell you directly.

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

Encourage collaboration whenever possible. Make sure your team has the right tools in place to be successful when working from home. Overcommunicate expectations so there are few miscommunications. And most importantly, make sure your people take time away from their desk in their home office. Also, be mindful of when you send an email to an employee. You’re the boss and if you are working during non-business hours and send an email to a staff member, they often feel obligated to respond. This can lead to an unhealthy relationship.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Be Kind…it has to be more than words. Create actions around it and actually execute small acts of kindness. It is known that it can go a long way in making the world a better place. Think about this. Was there a time when someone did something unexpected for you that positively impacted your day? When this happened to you, didn’t it feel like you were a nicer person for the rest of the day because of it? Didn’t it make you want to do something kind for someone else? Acts of kindness can be contagious!

There are so many ways every person can do this. You can send a kind email, a caring text, or leave a thoughtful voicemail. You can give others around you a small gift that is unexpected. Or better yet, just tell someone how much they mean to you. Any of these actions will have a positive impact on someone’s day and hopefully they are able to continue passing it on to the next. So, be kind…we need more of that in our world today.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Take pride in everything you do.” I share this with my executive team, my sales team and my family. I have 5 sons and I share this quote with them often as I want to teach them how to become good people and good men. This quote has been relevant in my life because it’s how I judge everything that I approach and do. A half-hearted approach provides a half-hearted result.

Thank you for these great insights!

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