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Jordan Rackie of Keyfactor: “Support the customer as they navigate internal hurdles”

Do your homework and ask the right questions during the discovery phase. Take the time to truly understand the problem the customer is trying to solve and some of the internal challenges they need to overcome. As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or […]

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Do your homework and ask the right questions during the discovery phase. Take the time to truly understand the problem the customer is trying to solve and some of the internal challenges they need to overcome.


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 Jordan Rackie.

Jordan Rackie is chief executive officer at Keyfactor (www.keyfactor.com), the 20th fastest growing cybersecurity business in America (Inc. 5000). He’s an expert in developing and leading modern go-to-market teams and strategy, having led multiple companies through large-scale growth, creating over 500 million dollars in business value along the way. Jordan’s previous experience includes SVP of global revenue at Tricentis, a globally recognized leader in software test automation and software quality assurance solutions, and chief revenue officer for QASymphony (merged with Tricentis), ranked by Inc. Magazine as the 8th fastest growing software business in the U.S. in 2017. He was also a sales leader and executive for Pardot (acquired by Salesforce). In 2020, Jordan was recognized as a Georgia Tech Alumni 40 under 40 honoree.


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’ve always enjoyed opportunities where I could adapt and relate to many types of people and ultimately provide value to individuals and businesses. I’ve felt a natural fit in sales roles at B2B companies and subsequently, that’s where I’ve spent most of my career as a global sales and operations leader, chief revenue officer and now, as CEO for an emerging cybersecurity technology company.

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?

Years ago, I spilled liquid on my laptop while on a study abroad program. The trackpad stopped working and I had to wait weeks to get a replacement. Out of necessity, I was forced to learn how to navigate my computer completely with keyboard shortcuts. While funny and frustrating at the same time, the lesson was invaluable, especially early in my career as an inside sales rep. Technology is an inside rep’s number one tool and knowing every shortcut helped me build efficiencies to get the job done faster. Today, I’m a big believer in efficiency and using the tools needed to be successful. If you’re a builder, you’ve got a toolbox or belt loaded with essentials to build fast. Similarly, as a sales rep, having the ability to work fast on a computer is essential and can help you get the job done faster than others.

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

As we know, diversity in the tech industry is a problem and it’s going to take a collaborative approach to not only ensure diversity, but also celebrate it. We’re taking a triangular approach to diversity at Keyfactor that includes an active initiative to increase and monitor diversity internally, ensure diversity through recruiting practices and working externally with a strategic non-profit to remove the imbalance between tech talent and societal demographics. We are confident that when launched, the partnership and initiative will become an industry standard to provide the tools and guidelines needed to expand diversity initiatives across other tech companies, too. This has been a passion project for the team and I, and we’re very excited for the official reveal later this Fall.

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?

I’ve been a big believer in the importance of having mentors internally and externally throughout our life — there are simply too many, I can’t name just one. My advice to others is to seek and surround yourself with people you admire, to bounce ideas off of and who relate to both your current role and the role you want down the road. Having peer mentors in areas of business that support your future aspirations who can provide ongoing support and expertise are invaluable when it comes to continuing to build your career path.

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

Sales is a number driven game; over the past 10+ years I’ve led sales team that have generated over a half billion in business value. I’ve managed sales teams at scale that have carried over 50m dollars in ARR annual quotas, and my teams have hit 22 of the last 24 board set quarterly targets.

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?

I’ve spent a good chunk of my career working in startup environments where the only certainty is uncertainty. There is no doubt that we’ve found ourselves in an uncertain time. At Keyfactor, one of our company’s core values is agility; more than ever, we all require an agile mindset and the ability to pivot and deal with variables on a daily basis. My advice is stay positive — work hard to embrace the new challenges that pop up every day. Look through a short-term, daily lens and treat those challenges as a chance to be nimble and make progress each and every day. Uncertainty is the new normal and we really have to try to embrace it as best we can.

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?

At Georgia Tech, I was fortunate to get some formal sales training but that said, it’s hard to replicate sales in a formal environment. Nothing can replace carrying a quota and handling the pressure that comes with that responsibility. My advice to people exploring a sales-based career path is to get out there and get as much real life experience as you can through internships or side jobs through college.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesy”, is assuming 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?

Personally, I’ve had a selling mindset that understands that for conversations to continue there must be a belief between the two parties that mutual benefit can be had.

In general, the best-selling strategy is complete transparency with the idea of mutual value between the business selling the product, service or technology, and the buyer who receives value through the purchase. From a transparency standpoint, if the buyer gives signals that the purchase will be valuable to them it then becomes a team exercise with the seller and buyer working together to ensure a mutual fit and internal positioning to move the deal forward transactionally and commercially within the buyer’s organization.

The team exercise involves the seller, who’s an expert in selling the product and providing the best practice motions on product evaluation and purchasing. That expert collaborates with the buyer, who’s an expert on their internal processes. That synchronization and team approach is ideal; if the buyer signals that the seller is being pushy, that usually indicates misalignment between the two parties. Together, the seller and buyer have to stay organized and ensure alignment on timelines and advancements to achieve synergy and avoid a breakdown in the process. Most often an alignment or communication breakdown is the root cause of a buyer feeling as though the seller is being too pushy or ‘salesy’.

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?

The way sellers approach and adapt to conversations is very important. As a seller, your approachability and ability to adapt to the individual that you’re talking to, combined with a high level of emotional intelligence, is critical in selling. You’ve got to be self-aware when assessing whether you’re on the same page as the people you’re talking to.

I always recommend taking an approach that’s based around your audience and working hard to see things from their side of the table. Make it less about selling something and more about solving a business problem.

I believe the best salespeople are exceptional at selling through product/solution steady state (versus just focusing on selling up to contract execution), which looks through a longer lens where the buyer receives value from their investment. Understanding desired outcomes and defining measurable success with the buyer is really important. Too many salespeople see the signed contract as the goal, but in actuality the buyer is looking to achieve a steady state vision of business transformation through the purchase. Continuing to ask questions downstream through the process that focus and reiterate steady stare goals are vital.

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?

Research is key in lead generation. That said, when entering the sales process, the first thing to understand is what you’re selling and whether you’re in a high velocity, transactional selling motion or a longer, more complex, enterprise sales cycle.

Strategy varies depending on what you’re selling. At one point, I was an SDR selling a mid-priced product. The strategy I used then required research and reading things that were relevant to the buyer. At the same time, I was cognizant that outreach was a volume play and hitting the appropriate outreach volumes was important. The approach changes if you’re selling a higher price-point product as the complexity of the sales motion will define the amount of research required.

A full cycle salesperson is expected to generate leads and close deals. The greatest tip I can offer is to block off time on your calendar that’s dedicated to outreach and prospecting. Make it a focused requirement. Sales reps won’t cancel or reschedule bottom or middle-of-the-funnel meetings and similarly, you need to work hard to make sure you’re not canceling prospecting time that’s earmarked for top-of-funnel development. The best salespeople I’ve worked with understand that they can’t be solely reliant on marketing leads and continuously work hard to fill the top of the funnel.

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’?

Handling sales objections should be straight forward for most, especially if you’ve done your homework. The nature of selling means that you’ve heard objections and questions before, and so you should have responses ready. If you get stumped by a FAQ or objection, that’s very often a preparation failure. But, that’s not to say that new questions outside the FAQ and standard objection list don’t arise, and when they do, sales reps need to know that it’s okay to tell the prospect that you don’t know the answer, and that you’ll find out and circle back. Take detailed notes, write down complex questions and check with experts for the answers. Taking the time to find the right answer, rather than stumbling through a response or making it up, is always the better option.

‘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.

Successfully closing a deal starts with the right level of preparation and establishing lines of communication and a team approach upfront. Bearing that in mind, I’ve always found these tips helpful:

1. Do your homework and ask the right questions during the discovery phase. Take the time to truly understand the problem the customer is trying to solve and some of the internal challenges they need to overcome.

2. Define shared timelines across yourself and the buyer. Establish key dates and milestones that pinpoint the compelling events that move the sales cycle to a close.

3. Work with the buyer to set measurable success measures for their company’s steady state, and what their vision of success looks like with your product or service in place.

4. Communicate and check in regularly, using the timeline and shared dates as a guide to keep the process moving.

5. Support the customer as they navigate internal hurdles. Share best practices and tools where you can to help them get buy-in from their internal stakeholders.

By far, the key to closing is tying back the close date back to a compelling event. Ideally that event is on the customer side and relates to project timelines or milestones. Ask about projects up front and at initial discovery. If you’re navigating a cycle without a compelling event, as the seller you need to work to identity other, potentially commercial timebound, incentives that creates the urgency required to forecast out. Maybe for the buyer, that becomes competitive advantage or revenue growth. Operate with the mindset that it’s in the buyer’s best interest to close, not us as the seller. Doing so helps you achieve success at selling through a steady state; closing becomes just one of the many milestones. If you can focus on that, meeting future dates and targets becomes easier.

Closing comes down to understanding the timelines of the buyer and creating time-bound incentives if you can’t pinpoint an internally compelling event — this isn’t ideal, but it helps to create urgency when needed. As a best practice, when an organization sets its prices, it reflects the true price and the market rate for your product or service; if the buyer seeks a concession or piece of value (e.g. price discount or change in payment terms) the selling organization should have ready-made levers they can pull that exchange value for value. For example, maybe your organization sees value in receiving multi-year payment up front, and that becomes a lever in exchange for a decrease in the annual subscription rate.

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?

When we talk about compelling events it’s like comparing pain killers to vitamins. There is a reason the pain killer market is 10 times the size as the vitamin market and that’s because people buy to solve for active pain much more often than to prevent future pain. Challenges in converting and closing leads is a symptom of having improperly identified what the pain actually is and what would compel the buyer to make a change or purchase. My recommendation to sellers who are struggling is to think of your value proposition and how it ties to the pains of your buyer’s business, versus selling it as a more of a preventative measure.

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?

By the time you reach the closing stage within the sales cycle the seller should understand how the buyer likes to communicate. Leverage that medium as a primary tool. If you find that your buyer isn’t getting back to you in general, that’s a clear indicator of possible misalignment on the perception of timing, or that you’ve worked your way into the ‘friend zone’ where they are afraid to give you bad or changed news. When it comes to seller and buyer communications, any news is good news, and you should let them know that early in the cycle. While you don’t want to come off as arrogant, you most importantly don’t want to come off as desperate and needing their business. People inherently love to share good news, but they also often want to avoid bad news or conflict. You need to let them know that if timelines ever shift on their end, that’s okay, and to just to let you know; it happens. Be clear on timelines and the importance of communicating changes so you have time to react and support your customer’s situation, and make them feel comfortable to share any news, good or bad.

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. 🙂

If I could influence a movement, it would be the broad embrace of the value of diversity in people and opinions. I’ve always focused on collecting a variety of opinions from a variety of people and believe that having an eclectic approach for reaching decisions is important to achieving success. The diversity movement has accelerated recently, and we need to continue that movement not just with lip service, but with a concrete understanding of the value in having a diverse workforce and how business benefits from embracing that diversity.

How can our readers follow you online?

On LinkedIn: https://www.linkedin.com/in/jordanrackie/

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

Thank you for the opportunity!

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