SalesTechStar Interview with Chris Calkin, Vice President of Sales, CircleCI

Making sure your message not only gets your prospects’ attention through the overabundance of information but that it is also uniquely interesting to them, is a true challenge today. Catch this interview where Chris Calkin, Vice President of Sales at CircleCI talks about his biggest tech sales moments and also dips into the biggest industry challenges that face sales teams today.

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Can you tell us a little about yourself Chris? We’d love to hear about some of your biggest sales learnings (and highlights) from your journey so far.

After graduating with a degree in Entrepreneurship, I started my career at a then 30-person marketing measurement startup. Even though it was an entry-level role, because it was a startup I was exposed and contributed to the international sales efforts (45% of our revenue at the time was international), as well as other areas of the business including legal, finance, product and marketing. A key turning point was when I made the decision to get organized. From there, my productivity skyrocketed and I quickly was promoted, eventually leading sales efforts for a new product line the company had established. From there, I decided to increase my business acumen via an MBA at Oxford. After completion, I pursued leading global sales at a growing technology company, which is what I’m doing today at CircleCI!

While there are innumerable highlights and learnings to choose from my experience, two stick out in my mind:

• In my prior time as a Senior Account Executive, I did numerous deals with major enterprises and rising startups, ranging from Starbucks to Uber, and many negotiations were extremely challenging. When I ultimately brought in a global MSA with Amazon and its subsidiaries, I learned the hard way that true procurement leaders can win by digging in on the ‘why’, working to their own timeline, knowing the solution deeply, and always keeping doubt in mind. Today, I teach my teams to make sure value is always clearly understood and acknowledged by all parties within a deal and that timelines and pricing are agreed upon as early as possible.
• Opening the Boston office for CircleCI and working with leaders I hired there to make it successful is an absolute highlight. Boston has a strong DevOps community and our solution was already well adopted by leaders like Boston Consulting Group. However, if it wasn’t for the entrepreneurial spirit and hard work of the folks I brought in to grow that office, and the quick and continuous culture we solidified, it wouldn’t have been the success it is today (grew from 10 to 28% of revenue within a year). Since then, I’ve had the opportunity to open offices and collaborate with new leaders in Tokyo, London, and Denver (where I sit today).

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Sales is a challenging role, one of the best ways to optimize the function is through recovery of lost sales opportunities- could you tell us about some of your most successful methods that have helped you recover lost prospects or opportunities?

The first and most important method is to deeply understand the “why” behind the loss. The most common “why” I’ve seen is that the deal simply lost steam, and folks on the prospect side simply stopped responding. Before re-engaging, map out the prospective customer in terms of personnel involved with the buying process, what their unique pain points are, and what commercial insights you have to offer each. From there comes the difficult process of getting their attention. Don’t ignore the fact that the sale was lost, use it to demonstrate what costs they’ve incurred since not making a decision. When you do get back to the discussion, be sure to have clear, metrics-driven insights and get a mutually agreed upon sales plan towards close (if we deliver X, you will deliver Y, on Z date). In my opinion, the most challenging part here is resparking that interest, so messaging, delivery, persona targeting, and timing are key.

What would you say are some of the biggest challenges technology marketers or sales teams in tech face today? How would you advise them to optimize their process or strategy further to prevent these common hiccups/challenges?

Paradox of choice, aka analysis paralysis, is one of the key challenges marketers and sales teams face. With the immediate availability of information for consumers combined with the increasing number of vendors in your clients inbox, voicemail, and LinkedIn, prospects are drowning in choice. Making sure your message not only gets your prospects’ attention through the overabundance of information but that it is also uniquely interesting to them, is a true challenge today.

Our teams at CircleCI leverage the Challenger Sale methodology, where we’re hyper-focused on bringing tailored commercial insights to our customers. If you can do this through creative channels and to a wide range of personas, you should be able to gain a foot in the door with a prospect with enough leverage to open it completely.

Establishing new market opportunities but also the RIGHT opportunities is crucial to the whole tech sales process- we’d love to know your thoughts on the best sales technologies and tools that have helped you here.

The most valuable tool in our individual salesperson and sales leadership tools is still LinkedIn Sales Navigator. Sales Nav has allowed us to not only reach the right audience with relevant data, but has also helped inform our territory strategy, sales targeting, and office expansion. As an example, before we opened our office in London and subsequently established our EMEA strategy, we heavily leveraged SalesNav data to inform us of the DevOps engineering presence within each country.

Gong.io is also a new tool our team is already getting valuable insights from. While our sales motion was already mostly done through Zoom, our ability to coach and collaborate on deals changed with the shift to complete remote work under COVID-19. Gong gave our managers and I granular and macro-level insights into performance so that we could quickly assist our salespeople and prospects in unique situations.

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Constant reskilling and development is important in today’s marketing and sales environment to help users and professionals cope with the constant evolution in martech / salestech. How do you approach this for yourself and your team?

CircleCI has established a best in class sales enablement team and culture that ensures our teams are continuously operating on the cutting edge. This involves OKRs (Objectives and Key Results) assigned to each sales leader specifically focused on training, regular incorporation of third-party sessions and speakers (Challenger adoption, MEDDPICC), and team member-led training sessions where we ask one person to bring their strength to the entire revenue organization.

What would you say are some of the top must-haves or best practices every tech sales strategy should consist of?

It starts with the basics: clear goals, rules of engagement, roles and responsibilities, and a demonstrated path of how to achieve. If your goals aren’t concrete and quantitative, it’s impossible to reach or exceed them. From there, you need to have a deep understanding of your customer. How do they operate, how do they typically make decisions, and where is there common need to improve? These all need to be documented and top of mind for each salesperson. The last should be an established management structure and leadership team that can show salespeople the right path to success without forcing a specific right way of doing things. I learned from early failures as a manager that not everyone’s path to success in sales will be the same as your own.

How according to you will the typical role of tomorrow’s B2B/Tech sales person evolve, given the dynamics and innovations in SalesTech? What should today’s sales person do to prepare for a future role as a senior level Sales executive in tech?

The current climate as a result of COVID-19 has amplified trends that already were growing in sales. If your teams aren’t already doing a significant percentage of their sales through call/video, they will (and should) be. Given the amount of information that’s out there and available for everyone, our sales teams need to stay on the cutting edge of market trends important to their industry to stay valuable to their customers and help improve their product and service. In addition to the recurring learning initiatives we have, we also have established certifications to ensure continuous knowledge. If you’re in sales and wish to not only succeed in the short term but grow your career (as an IC or manager), learn about business principles. The better you understand marketing, finance, legal, product and engineering, the better you’ll be able to navigate and provide value to your company and your customers.

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What would you say or do in your capacity to turn Sales and Technology sales (or marketing) into the most exciting job of the decade?!

At CircleCI, we’re helping businesses accelerate their delivery of value through software. This might be through working with Facebook on their open-source machine learning library Pytorch, or working with a company developing low-cost ventilators to help COVID-19 patients in the developing world. For me, this is the most exciting place to be and I believe many technology sales organizations have the opportunity to put themselves into that situation. A career in tech sales gives you the opportunity to run your own book of business and deeply understand a wide range of companies and industries, constantly exposing you to new challenges or technologies.

Tag (mention/write about) the one person in the industry whose answers to these questions you would love to read!

Mike Weinberg’s approach to sales is straightforward, works across industries, doesn’t sugarcoat the work, and celebrates the hard stuff. It would be great to see his answers.

Your favorite Sales/SalesTech  quote and sales leadership books you’d suggest everyone in Sales reads:

“There are no shortcuts to knowledge. Following conventional wisdom and relying on shortcuts can be worse than knowing nothing at all.” – Ben Horowitz, The Hard Thing about Hard Things

 “Either run the day or the day runs you.” – Jim Rohn

Books: New Sales Simplified, The Challenger Sale, How to Win Friends and Influence People, 48 Laws of Power, Extreme Ownership, The Lean Startup, Crossing the Chasm, The Art of Negotiating the Best Deal

A few last thoughts/ tips for sales and marketing teams (businesses) trying to navigate through the current pandemic crisis.

• Don’t use COVID-19 as a reason to stall or closed-lost deals. COVID-19 is impacting you and your customer’s business, but the impact depends on many factors. Some businesses may be truly financially decimated, others may simply be uncertain about the future, and others may be seeing a lift. Get to know this reason and then work to progress accordingly.
• Stick to your value but be flexible on how you can deliver it. We don’t need to be giving our products away, but we might need to be more flexible on the logistics of the value delivery than we were before.
• People are at home. They are busy, but if you are bringing value to them they will be happy to have a conversation on how you can actually help
• Stay personally accountable and rise above using the pandemic as a personal excuse. Your job may be different now than it was, but it’s on us to navigate through it, not let it defeat us.