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Tip Fairchild of SquadLocker: “Introduce creative solutions”

Introduce creative solutions — The more creative your initial proposal was the better chance you have to close. If something stuck out over the others during the closing process, it is usually front of mind for the prospect and might be what gets them to take the leap. As a part of my series about how to be […]

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Introduce creative solutions — The more creative your initial proposal was the better chance you have to close. If something stuck out over the others during the closing process, it is usually front of mind for the prospect and might be what gets them to take the leap.


As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Tip Fairchild.

Tip Fairchild rose to baseball stardom at Monmouth Academy and the University of Southern Maine, and then to the professional ranks as pitcher in the Houston Astros organization. During his baseball career, his mind, drive, and compassion always matched, or perhaps even surpassed, his arm. When he retired after the 2009 season, he turned his sports experience into a successful role as corporate sales strategist. He joined SquadLocker, a company that provides online tools for teams, organizations, and schools to manage custom apparel and equipment purchasing and is currently Director of Sales. Tip is an avid user of SalesForce and powerful data during and after the initial sale. His specialty is developing sales processes from introduction of a lead to execution of a sale and beyond.


Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

I grew up in a small town in central Maine called Monmouth where I played a lot of basketball and baseball. My goal was always to play at the next level. I played baseball at Monmouth Academy, then the University of Southern Maine, and then was drafted as a pitcher by the Houston Astros. I had Tommy John surgery on my elbow in 2007 after having a great season in 2006. I played for a couple more years, but the feel was never quite the same as before the surgery.

I finished my business degree from USM during the off seasons and my mind was ready to enter the business world. The body soon followed as I just could not get my arm ready for another spring training and 150+ game season.

I always loved gear and loved to learn about brands that were available. I had moved to Rhode Island from Maine to live with my girlfriend (now wife, and we have two beautiful daughters). I took a chance walking into the SquadLocker office in 2010 and met the CEO and founder, Gary Goldberg. I told him that I might be able to help sell his product, as they were selling pretty heavily into the team sports space. He didn’t have a job available at that time, but took a shot, as did I, and we have been working together ever since in the textile consumer goods space.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

Sure! I think the most interesting part of my career journey is how it started. I mentioned this in my back story, but to elaborate a little more, I was coming off my first career which was an athlete playing professional baseball for the Houston Astros organization. I had my business degree, and it was time to shift gears. I took a chance and walked into a building that was doing something I related to. I’ve been with the company for 10 years now. The lesson learned was to just take a shot. Everyday there is always something hard to do on your plate, and half the time it is only hard because you are telling yourself it is. Just jump.

Are you working on any exciting new projects now? How do you think that will help people?

We have been working hard on “our why” at SquadLocker. Gary Goldberg, our CEO and Founder, has developed a message that we believe helps not only people, but the world. The coaches and administrators who we help are here to mentor the youth and help them on their journey to adulthood. With strong mentorship, these kids become valuable citizens who can improve the world. We cannot coach every kid, but we hope to free up these coaches so that they are able to teach, coach, and mentor our youth. We want them to put their time into what matters most.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My parents, both being educators, were extremely instrumental on my path. Not only for the support during my professional athletic days, but toward how I was able to transition into my next phase. Early on in my career, Nellie Tillinghast, who is still with the company as Director of Enterprise Operations, showed me how to conduct my business in an organized fashion. I am extremely organized in my personal life, but I was not sure how to replicate that stepping into the business world. Even managing an inbox was a task I was not quite sure how to take on. Nellie helped me understand the importance of data early on, and a term that has stuck with me for a long time has been “data hygiene.” Making sure my SalesForce or CRM work, along with Inbox management, and using tools to help be more efficient not only day to day, but task to task has helped me tremendously in my career. I owe that to early days working with Nellie.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

I haven’t been in just one type of sales role. I have been on the direct side, as well as through distribution — two completely different sides of selling. I started in Inside Sales, pounding away at the phones, also doing some sales development work at that time. From there, I became an Inside Sales Leader. After that, we built some teams and started new verticals within the company. We had to prove a concept and what type of selling would work in that space. During that time, I was Director of Business Development. Now, I am the Director of Sales and handle direct and indirect selling for SquadLocker. We have a number of different divisions within the sales group, and my career has led me to help understand the different functions of those roles.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

My demographic was hit very hard with anxiety due to drastic change in lifestyle. My wife and I have two young daughters (6 and 4) and were not only required to work from home, but also educate from home at the same time. It was difficult. There were days that you wanted to throw your hands up in the air, but there were still professional and personal tasks to be done. I work really hard with our teams on routine. We put together different series of check-ins so we could keep the personal relationships going, along with the work. As a family, we tried to do the same thing. Keep a routine, schedule check-ins, and look out for each other. At the same time that we were trying to keep a routine, some days it just wouldn’t go as planned. We had to be “ok” with that, and I think being versatile and able to change on the fly was a skill that had to be learned during this time. Also having a partner who understands was crucial. My wife has been a rock star with scheduling and making sure that we were “where we needed to be.”

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

I think our education system assumes that being in sales is just something that comes naturally to people, especially extroverts. We also assume that people know how to manage finances, select a mortgage, and write a check, but we do not clearly educate our youth on those either. I learn things every day regarding sales, and constantly find myself reading, watching videos, or taking a course. Our CEO (Gary Goldberg) and I just took a class that was offered by the Kellogg School at Northwestern on Mastering Sales taught by Craig Wortmann. It was such a great refresher for things that we might have learned, or picked up somewhat on our own, but maybe have missed certain points along the way. Negotiation skills are vital in life, not just in work.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesy”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

Being “salesy” is probably better defined by being persuasive. Being persuasive can come with potential negative connotations. There is no question that using persuasive selling techniques can feel pushy to most people and make them feel uncomfortable. At SquadLocker, we work to educate our salespeople on becoming “trusted advisors” to our customers and prospects. We want them to understand that we are the product experts. We have done it thousands of times, and here is the roadmap that we take people on to experience success together. I believe that using the term “trusted advisor” with our sales team has slowed down their pitches and gives them a more comforting tone during their calls and how they write emails. It is designed to be more calming, and our customers feel that way working with our group.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

My best is uncovering the stakeholders during the sales process, which probably falls into a couple of these categories, but starts with prospecting. Understanding where the decision-making process lives is so undervalued. You can go through all of the stages listed above perfectly, but if it is to the wrong person, or group of people, it was wasted effort. Asking strong blue-printing questions early in the process leads to greater success. Knowing how the buying process is done and timetables is so often overlooked. Follow-up is a close second for me. So often sales people forget the follow up. We have installed some great tools like outreach.io to assist with this process. You do not want it to feel like you are “checking in on the deal,” but more of a trusted advisor feel discussing the timeline you have reviewed earlier and keeping them on track.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

It starts with a great marketing team. Strong account-based marketers help make the time you are spending with people on the phone already pre-qualified. One of the conversations I tend to have early every day in stand ups with our BDR and SDR groups is regarding qualified lead scoring. What quality were the calls the day before and getting examples of weaker quality leads to our marketing team right away so they can make adjustments on the fly. Our Director of Marketing, Matt Desilet, has a great grasp of this concept and his team is able to turn on a dime to help us speak with the people who can help our company grow the fastest.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

People hate hearing “no” or hearing reasons why their solution might not be a winner. It is hard for people to deal with this only because they typically do not want to. We really try to train on objection handling by building out scripts and objection handling battle cards for our different sales groups. We also try to expose the pain points the customer currently has early in the conversation. Once we are able pitch them what the future state can look like, it is tougher for them to object and go back to the pain they already have exposed. When they do, we can lean into those early exposed pain points with solutions that help solve them.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

  1. Listen — The prospect is going to tell you what they need to happen to get it done. You need to ask, and then listen to their response. I love to use the phase, “under what circumstances?” Everyone has a circumstance for any decision. Once you ask, you usually get an answer. From there, the ball is in your court to whether you can execute on it or not.
  2. Take amazing notes — Rely on your previous conversations. I like to dig back into small things that might have come up early on during even the blue-printing of the decision makers. Talking about their favorite sports team or asking about their daughter’s dance recital that caused them to push the meeting for the previous week are great ways to show them that you “heard” them. If you are dealing with many clients, the only way you will remember these things is by writing them in a CRM tool. My program of choice is SalesForce.
  3. Be Trusted — Do not just feel like a trusted advisor. Be one. There is a difference. It is being impeccable with your word, having bottled enthusiasm, and knowing that you have done this before. Exuding confidence on the closing calls is different than arrogance or cockiness. It is a fine line, but the more you seem comfortable with moving forward, it starts to rub off on the prospect.
  4. Remove Pressure — As tough as this is to do, pressure is what ends up causing mistakes during your process. You can get sloppy and rush when you are feeling like you are up against quota or a deadline. It rubs off in the way that you are selling and can give a “pushy” feel. I always try to work on my cadence and tonality while speaking. Those two things are extremely valuable for getting specific points across, but also help keep my heart rate down. If I can take some breaths in between sentences and pause a little, it feels like everything slows down. I have taken the same skill that I used when pitching in pressure situations and installed it in the sales process.
  5. Introduce creative solutions — The more creative your initial proposal was the better chance you have to close. If something stuck out over the others during the closing process, it is usually front of mind for the prospect and might be what gets them to take the leap.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

Following up is forgotten by so many salespeople, especially ones who lack poor organizational behavior. Consistent follow up is so important, but it cannot come off as “checking in” all the time. Checking in feels pushy, like you are begging for the yes or no. When I see something that make me think of someone, I like to share those things with them. It could be as easy as a sports score, or an article that they might like. I think quick videos are great as well. Sending a LinkedIn message that has a one minute video that reminded you of one of the conversations you have had is a great way to follow up with someone.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

We have good salespeople who might execute an enterprise level sale through our chat feature and never hear the other person’s voice. I would not avoid any communication method. More importantly, I would use the communication method that the prospect feels most comfortable with. They might not want to feel trapped on a Zoom call but are very comfortable working through email. Adapting to their communication method I would consider to be the “best.”

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

Being in the sports world, I think it is very important to give access and opportunity to our youth to be able to participate. Being able to participate in organizations in their community not only helps them live healthier lives but starts to build a foundation around teamwork and their communication skills. Our interview was related to being a great salesperson but not sounding too salesy. Those negotiation skills start with playing stickball on the playground and deciding who is going to bat first!

How can our readers follow you online?

https://www.linkedin.com/in/tip-fairchild-66608821/

Thank you for the interview. We wish you only continued success!

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