Alex Dripchak of Commence: “In sales, emotion always trumps logic. And “salesy” is not an emotion that people want to feel from others”

In sales, emotion always trumps logic. And “salesy” is not an emotion that people want to feel from others. So if you don’t have emotion on your side, you effectively have nothing. People will put their guard up, if not flat-out shut you down, and then move on to one of the 75 other folks […]

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In sales, emotion always trumps logic. And “salesy” is not an emotion that people want to feel from others. So if you don’t have emotion on your side, you effectively have nothing. People will put their guard up, if not flat-out shut you down, and then move on to one of the 75 other folks clamoring for their business.


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 Alex Dripchak.

Alex Dripchak is a sales and career-readiness adviser based in New York City. A relationship manager at Mercer, a global HR consulting leader, he previously worked at Oracle, where he was the first person to be a sales manager and outside producer by the age of 25. He is the co-founder of Commence, a college-to-career academy, and the author of “100 Skills of the Successful Sales Professional” (Business Expert Press, June 2021).


Thank you for talking with us. Before we dig in, tell our readers the backstory on how you came to this career path.

Like many in the sales profession, I fell *** backwards into it. I had done three internships in the areas of media, marketing, and advertising, and naturally wanted to go into marketing — not sales. In fact, it became a running joke with one of my roommates, who after hearing about each one of my opportunities would say, “Sooooooo… sales?”

Ultimately, it came down to my walking by a career fair, seeing a banner out of the corner of my eye from a company I was already interviewing with for a different role, continuing past the career fair, walking down some stairs, second-guessing myself for not stopping by, walking back up those stairs, and then… BAM! It was the beginning of my career. Four years later, I had gotten four promotions in sales at that same company: Oracle.

I often wonder what would have happened if I had just kept on walking that day. It’s interesting how we are constantly one step (literally in my case) or decision away from a completely different life.

What is one of the most funny or interesting stories in your career so far? And what was your lesson or takeaway?

One of my most memorable (and, in hindsight, funny) stories is from early in my career. A lady, who I’ll call Janet, would take my countless sales calls with such intense trepidation that it was hard not to feel bad for her. I could hear Janet’s hard swallows, deep breaths, and trembling voice every time I called. It seemed like a setup for a horror movie more than a partnership evaluation.

The running joke around our office was that every time I called Janet, I was like a hypnotist who would eventually put her under my spell. For “Get Out” fans, it was like teacup time. At last, she would be coaxed into buying my solutions.

This funny yet somewhat sad realization was one of my inspirations for writing my new book — to help demystify and destigmatize the sales profession.

What new projects are you working on right now, and how do you think they’ll help people?

One project is publicizing and promoting my new book and, specifically, to assuage people’s fears about going into sales and to spell out the skills it takes to be successful. If such skills seem to align with who you are or who you want to be, by all means, consider sales.

There are enough sales experts and methodologies out there today, so in writing my book, I wanted to take an altogether different approach and both curate and rank the most impactful tidbits from others. This way, I could give folks a flavor for developing the right skills and growing both personally and professionally.

Also, my current passion project is a college-to-career coaching and skills-development program, which I co-founded to teach students our professional, financial, and social “I wish I knew that earlier” lessons. I believe that if you start young people on the right path early enough — before they are thrust into the working world — you can safeguard their success.

No one is able to achieve success without some help along the way. Tell us about someone that you especially appreciate and, if you like, share a story about them.

My managers, VPs, and mentors along the way have been instrumental in my success, whether they were murder-boarding my proposals and presentations, flagging flaws or skills gaps, celebrating successes, or spotlighting my potential. There are, however, a few people to single out, as they’ve been critical to my development: Mark Ringuette, a manager, peer, and friend; Graham Douglas, a former VP and dissection genius; and John Donahue, a director with a relentless work ethic. Also, I’d be remiss if I didn’t mention Kieran Cunniffee and Scott Catherwood, who recognized my tremendous aspirations.

A story that I vividly recall is the day that I was mysteriously summoned into Kieran’s office, and having no idea as to why. Little did I know that he would be offering a 24-year-old me a role as sales manager. I was in such disbelief that it felt like the room was spinning. The position had been vacant for more than a year, and some of the people that I’d go on to manage were up to twice my age. That moment was a real bright spot, and showed me that sales may very well be the right career for me.

Tell us how you’ve come to be an authority on sales.

I don’t know if I’d go as far as to say that I’m an authority on the topic, but I am a voracious student of the game. I also have a background in writing, going back as early as my high school and college days. These two things, coupled with my extreme action orientation, candid consultative approach, and intense focus on others, have served me well in my career and created opportunities for me to shepherd others.

Now let’s move into the main part of our interview. Almost any profession that a person enters will involve some form of sales. Still, most people have received no formal education on how to effectively sell. Why is it that the U.S. education system teaches nearly every other arcane subject, yet totally ignores sales, one of the most useful and multipurpose skills in people’s work life?

If I could hug you right now, I would!

Not only is my book geared toward young professionals, many of whom are dissuaded from pursuing a career in sales, but also my college-to-career program teaches skills such as persuasion, negotiation, presentation, and storytelling. So your question relates to an issue that I think about almost every day.

My firsthand experience continually confirms my anecdotal murmurings: sales is perceived as a dirty profession among “esteemed” educators. It is, and always has been, looked down on. And this stems from a societal tendency to lump all sales into the “greasy used-car salesman” category. As a result, most people remain unaware of the level of skill, education, and prestige involved in many sales roles.

But it’s important to realize that educators are not employers, a distinction that many of them take tremendous pride in. Moreover, while 88% college students say their number-one goal is to get a good job, less than 1% of funding goes to the Career Center. (Let me say that again: LESS THAN 1%.) This disconnect is a travesty. And it also says that we need to take educators’ viewpoints with a gargantuan grain of salt.

Yet, despite my fervor on this issue, I take solace in the fact that this issue isn’t all sad songs. Today, there are 57 U.S. colleges and universities that offer a sales major and plenty more with a sales concentration or unofficial coursework.

So we are making strides in this regard, especially as leaders in higher education face increasing headwinds and outside pressures and perspectives. But the sooner we can turn our incremental steps into exponential leaps, the better. Then we can teach students these, as you say, useful and multipurpose skills.

The title of our discussion is “How to Be Great at Sales Without Seeming Salesy.” This makes an assumption that being salesy is something negative to be avoided. Do you agree, and whether you do or don’t, can you explain why?

I am in lockstep with this belief. And it’s sad that while the words “sales” and “salesy” is only one letter apart, they are vastly different in areas like approach, process, and language. Now if you happen to be in a more transactional type of sales, you might get by with some salesy-ness, but it’ll never work in a more complex sales cycle.

In sales, emotion always trumps logic. And “salesy” is not an emotion that people want to feel from others. So if you don’t have emotion on your side, you effectively have nothing. People will put their guard up, if not flat-out shut you down, and then move on to one of the 75 other folks clamoring for their business.

The seven stages of a sales cycle are usually broken down into prospecting, preparation, approach, presentation, handling objections, closing, and follow-up. Which stage are you most personally skilled at, and what is your secret sauce?

I’d say that presentation is my strength and, in particular, that exceptional preparation, detail orientation, and contingency planning are the key reasons I continue to excel. In finalist meetings, I currently have a 100% selection rate in my present role.

As for my secret sauce, I deconstruct a time limit for my presentations to offer both flexibility and choreography. For one recent finalist meeting, my colleagues and I knew that we’d have 14 people in the room, with a lot of ground to cover across our company’s entire Benefits spectrum. And in doing our homework up front, we also learned that the COO, who would be in attendance, is especially inquisitive and that we should plan accordingly.

In our team’s rehearsals, we adhered to 85–90% of our allotted time, with our section leads planning for both full and consolidated versions in case we were running low on time. This proved to be a good thing, as the COO, who we had expected to ask eight to 12 questions, asked closer to 15. By having multiple versions of our presentation planned, together with drop-dead times per section, we were assured that we’d be able to cover everything.

Our audience was so visibly impressed with our fluidity and cohesion that I was promptly convinced that we’d be confirmed within two days. Still, I was repeatedly told that things work differently in Benefits, so it’d be at least one to two weeks. But no more than an hour later, we got word that we were verbally selected. Better yet, the client made it official just two days later.

Prospecting is a basic step of the sales cycle. While every industry is unique, what are some universal strategies that can generate good, qualified leads?

I make it a point to learn what’s most valuable to my client, and then, regardless of how it ties into our work, I lead with that. Prestige offers, such as closed-group roundtables and executive alliances, have proved to be particularly valuable. A critical caveat, however, is to avoid doing this in a way that could be perceived as desperate or pushy. I simply extend the offer or invitation and make sure to communicate how desirable or in-demand it’s been for others. My most effective outreaches have been either personally apropos (usually in a client’s first 100 days in their role) or especially exclusive and powerful.

Why do you think that handling objections is difficult for most people? And what would you recommend they do to improve?

Personally, my mindset is that objections aren’t something to overcome or neutralize, as this tends to set up a more adversarial approach. I view objections as questions that simply require me to better prepare. This way, I can create a more positive, accessible frame with clients.

I think back to my sales days at Oracle, mastering the objection-handling playbook and putting it into practice in the real world. I had a conquer-not-clarify attitude, and took great pride in neutralizing objections. But the longer I’ve been in sales, the more I’ve learned to appreciate objections, as they usually signify a sincere interest. In fact, 9 in 10 clients, when not interested, won’t even bother raising objections or asking hard questions.

So I recommend that people consciously work to embrace hard questions, seek clarification or understanding, and answer candidly. Clients appreciate transparency a lot more than they do slick or canned objection handles.

Now, for those rare 1 in 10 clients who aren’t interested and, instead, are just looking to ruffle feathers with red herrings, I suggest checking out the “PAIS” system (Pause, Acknowledge, Ignore, Save) from sales trainer and author Jeb Blount.

Closing is the holy grail of sales. What are a few specific things that anyone can do to close a sale without being perceived as salesy or pushy?

For starters, don’t close. If you have differentiated yourself and added significant value at each stage of the sales cycle, you shouldn’t need to employ closing techniques.

After that, I’d refer people to the landmark study on closing sales conducted by psychologist Neil Rackham, the author of “SPIN Selling” and the founder of Huthwaite, a research and consulting firm. Rackham and his team spent 12 years observing over 35,000 sales calls and gathering data. They dissected the interactions to determine the most important components of a successful sale and how to put them together to increase the likelihood of success.

Rackham’s findings would go on to turn conventional sales wisdom on its head — revealing that three major beliefs about sales were misconceptions. The first and perhaps most important misconception: “Always be closing.”

So here are four good, alternative frames to closing.

First, use the client’s committed timeline to drive home the issue of need. Work backwards, step by step, to underscore the need to adhere to their timeline.

Second, focus on mitigating the usual client concerns, such as switching costs and buyer’s remorse, as opposed to just driving home the great features and benefits of your solution.

Third, showcase how your solution can help your client avoid a loss, not just recognize a gain. This is important because, by and large, clients are far more fearful of a loss than they are focused on recognizing a gain.

In this regard, my interactions with students are Exhibit A. Most would choose to do a single homework assignment — which is an infinitesimal fraction of their GPA, which ranks a lowly 12th on employers’ most important hiring characteristics — rather than go to a networking event, where just one such event could literally change their life. All to say, they favor avoiding a loss (a bad grade and disappointing a teacher) over recognizing a gain (the potential of finding a fulfilling, financially fruitful job).

And finally, fourth, increase the total number of people your client is saying no to. If you have taken a multi-threaded approach, including getting buy-in from their peers and introducing them to your own colleagues and senior-level executives, they’re no longer just saying no to you; they’re letting down their team, as well as yours.

With regard to follow-up, a lot of businesses get solid leads, yet nothing ever seems to close. What’s your advice to corporate leaders about following up and creating a successful conclusion without appearing overeager?

Find parallel streets to travel down. For instance, to include a prospect in things like seminars, webinars, white papers, or special events can be valuable to them. And while such actions don’t qualify as a direct follow-up, they may be even better. They say to a prospect “I value helping you” while, at the same time, perhaps nudging them to think: “That’s right. I need to get back to Yitzi soon.”

If a prospect won’t engage on these parallel streets, chances are your follow-up is significantly behind or they are not the real decision maker. This is the time to check with your prospect champion (or a colleague or mentor if you don’t have a prospect champion) to determine how you should pivot.

If it’s time to force a decision one way or another, one approach is to send an email with a sentiment like “Closing the Books” in the subject line. In the body of the message, you can express empathy with their situation and then ask a direct question: Should we remain in touch about XYZ?

Additionally, you can reiterate that, like them, you have numerous clients to serve and thus wonder if you can be of assistance or if may be time, in each other’s best interest, to agree to move on. Also, rather than sending the email yourself, ask someone from your company’s leadership team to do it. This elevates your prospect in status and could also lead to a more frank discussion.

There are so many communication channels to choose from today — email, texting, telephone, videoconferencing, and in-person, chiefly among them. Are there any channels that you’d recommend avoiding when trying to close a sale or do a follow-up? And which ones do you think are most effective?

I think that texting may be the best channel, especially when it comes to relationship building. So if a client is open to text messages being their primary mode of communication with you, that’s great. It is not only personal, but also fast and response-driven. As a caveat, however, don’t float the idea of texting after an initial introduction. Very few clients want to engage in this way so early in a relationship.

I have two clients that I text with regularly. One of them has selected our company at every organization he’s worked at. And the other one is currently approaching his 16th deal with us in less than a year. I rest my case!

We’re nearly done, so here’s a final question. As a person of enormous influence, if you could inspire a movement that would bring the most good to the greatest number of people, what would it be?

I bet that you already know my answer!

I’d inspire a movement to close the gap between what both employers and students want — and what educators actually provide. I am actively working on this now and hope that it creates some ripple effects out there to enable and empower decision makers to push education to the precipice.

How can our readers follow you online or on social media?

Thanks for asking. My primary platform is @areyouworkforceready on Instagram, but LinkedIn at either “Commence” or Alex Dripchak also works.

Thank you, Alex. We wish you continued success!

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