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“Why follow up is important.” With Mitch Russo & Chase Roberts

Position yourself on the same side of the table as your customer. In this hypothetical, you’re not sitting opposite your customer but rather next to them trying to see what they see. Employing customer empathy helps you understand if an objection stems from not fully demonstrating problem-product alignment or from some other variable you haven’t […]

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Position yourself on the same side of the table as your customer. In this hypothetical, you’re not sitting opposite your customer but rather next to them trying to see what they see. Employing customer empathy helps you understand if an objection stems from not fully demonstrating problem-product alignment or from some other variable you haven’t identified yet (i.e., budget authority, an internal naysayer, etc.). Understand the source of the objection and you’ll better understand how to handle it.


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 Chase Roberts.

Chase is a Principal at Vertex Ventures US, where he invests in early-stage B2B startups. Chase started his career in finance (Venture capital/private equity fund-of-funds and equity research) before seeking to join a venture-backed technology firm. This led him to Box, where he held sales, channel, and commercial partnership roles. Following a 5-year tenure at Box, Chase joined Segment, where he helped start the business development team and launch a startup program. Originally from Oklahoma, Chase graduated summa cum laude from the University of Oklahoma with dual degrees in Finance & Entrepreneurship/Venture Management. Chase earned his MBA from the University of California, Berkeley, Haas School of Business.


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?

The backstory is long, so I’ll share the CliffNotes version. After growing up in a small town in Oklahoma, I discovered tech startups in my early twenties and decided I wanted to orient my career toward the magic that emerges from Silicon Valley. After a couple of fortuitous runs as an operator at two successful software startups, I moved into venture capital at Vertex Ventures US (where I work today).

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?

When Inc. Magazine was doing a photo shoot of Aaron Levie, co-founder and CEO of Box, for Entrepreneur of the Year, they needed someone to chat with him so he’d look natural in the photos. Aaron grabbed me since I was the closest person nearby, and our conversation led to special projects and earning a front-row seat to his mind. The lesson? Recognize serendipity as it happens and embrace those situations.

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

As a venture capitalist, I’ve recently been exploring the next generation of enterprise software. Specifically, I’m considering how applications will become more data rich, the role of AI, and the software evolution that corresponds to the changing nature of how we work.

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?

Where I’m at today is largely the product of many people who helped me along the way. Aaron Levie. Chris Penner. Eric Purcell. Fede Menapace. Adam Carr. Chris Medeiros. Sandeep Bhadra. They’ve all created meaningful junctures that pushed my career forward in considerable ways. Carla Harris (vice chairman, global wealth management and senior client advisor at Morgan Stanley) once said the most important people in your career are your advocates, not your mentors. Since many career moves depend on the decisions made when you’re not in the room, it’s your advocates who create opportunities on your behalf. All of those mentioned have been advocates for me in my career.

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

Call it good luck — I’ve worked closely alongside so many talented salespeople that my experience is really an amalgamation of that of my colleagues. I started my career in tech doing inside sales at Box. Having joined Box early on and experienced the company through hyper growth, I got to see what good selling looks like at multiple stages. I focused on channel sales during the latter part of my Box tenure, which made me co-pilot to many of Box’s most savvy salespeople on hundreds of deals and gave me a macro-organizational view as I worked with sales leadership on partner strategy.

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?

There’s no easy answer, and anything I suggest is likely an imperfect solution. Gratitude can be a useful remedy for anxiety. Try writing down two things you are grateful for every single day.

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?

The education system is organized around research of which teaching is a by-product, and perhaps, largely a mechanism to fund more research. Research tends to follow the money, of which only 4.7% comes from businesses. The majority of funding actually comes from the federal government. Until the Department of Defense or Health and Human Services want research about sales, it’s unlikely that sales will emerge as a subject in higher education. Conversely, I bet we’ll start to see vocational programs emerge online teaching entry-level sales techniques.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesey”, 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?

This assumption is misguided. If it’s true that the product solves a problem that a buyer also hopes to solve, then it’s the salesperson’s job to help the buyer perceive that alignment (what I call “product-problem alignment’). Once product-problem alignment has been demonstrated — this often involves some form of a proof of concept — then salespeople are obligated to ask for the money. A quote that sticks with me came from an account executive at Box, Dan Cutler, with whom I worked on a handful of deals: “I’ve earned the right to ask for your business.” Dan seemed to view his sales cycles as a spectrum along which he had or hadn’t yet earned the right to ask a customer for their business. Once he had done so, he pushed for the close. Waffling wastes the time of all parties involved.

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?

I regularly see novice sellers lead customer calls by “showing” instead of “asking.” Salespeople falter when they talk about features and then wait for the customer to draw conclusions. Instead, salespeople should be deeply curious about the problem their customers hope to solve or in, many cases, don’t realize they have yet, and then partner with them to identify product-problem alignment. This starts with thoughtful discovery. Good discovery isn’t asking which features your customer likes best but rather digging into their requirements and then demonstrating how your product may or may not meet those requirements.

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?

A dollar spent on product marketing is as consequential as a dollar spent on product development. Product marketing is the practice of translating the value of your product into language that makes it easy to understand the value it will produce. Great lead generation starts with great product marketing. If prospects can self-qualify according to the story you’re telling about your product through marketing, then you are more likely to generate highly-qualified leads.

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’?

It doesn’t have to be hard. Position yourself on the same side of the table as your customer. In this hypothetical, you’re not sitting opposite your customer but rather next to them trying to see what they see. Employing customer empathy helps you understand if an objection stems from not fully demonstrating problem-product alignment or from some other variable you haven’t identified yet (i.e., budget authority, an internal naysayer, etc.). Understand the source of the objection and you’ll better understand how to handle it.

‘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.

Rather than call out 5 specific things, I’ll instead opt for a few principles that should underlie every stage of the process so that you earn the right to drive a close when the time is right.

  1. Be curious — ask questions before giving answers.
  2. Be complete — consider every variable that could influence a sale.
  3. Be the authority — demonstrate that you understand the problem space such that you’re qualified to guide your customer toward a solution.
  4. Seek evidence as proof — don’t rely on soft assumptions to make the case for problem-product alignment.
  5. Be direct — don’t dance around conclusions or assume consensus on where you might be in the sales process. “If I demonstrate X, Y, & Z, will I have the right to ask for your business?”

If you employ these principles throughout the sales cycle, you should feel confident asking for the customer’s business.

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?

“Follow up” falls more into organizational strategy: assigning responsibility to upholding customer commitments, developing a timeline and process for doing so, and clearly communicating with the customer along each of these dimensions. As long as you’re operating according to the expectations you’ve set forth, then the customer shouldn’t perceive overzealousness.

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?

The one that should be avoided is the one that won’t compel your customer to a close. Everyone has different preferred modes of communication, so try to understand which one is the most effective for your customer early in the sales process. For example, I opt for in-person communication or video calls in most situations. My wife, on the other hand, prefers written communication and would retract from a salesperson insisting on in-person meetings.

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. 🙂

Well, if we’re speaking literally about bringing the most good to the greatest number of people, my answer would have to be related to addressing climate change and embracing globalization. At a more abstract level, I’d say teach everyone on Earth how to have an honest discussion about the power of ideas.

How can our readers follow you online?

I’m on Twitter @chsrbrts and feel free to email me at [email protected].

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

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