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A Conversation with SalesLoft CEO, Kyle Porter
Kyle Porter Salesloft
By John Barrows | February 25, 2019

I couldn’t be more excited for SalesLoft’s upcoming Rainmaker19 conference held in Atlanta on March 11-13th. This is one of my favorite conferences of the year put on by one of my favorite companies. Their CEO Kyle and I connected back in the early days of both our businesses and I’ve been a huge fan of him and the company he has built ever since. They just do things right. They have a great technology that solves a problem for sales reps and organizations, an incredible internal culture that breeds excellence and a strong desire to help their customers succeed.

“Sales done right” has always been our “Why” here at JBarrows.  We believe that when sales is done right, it’s the greatest profession in the world, but when done wrong it’s the worst. SalesLoft aligns with this perfectly in that they do sales right themselves, while trying to make sure their customers do it right as well. For Rainmaker19 I’m excited to see what’s next for SalesLoft and their platform, while connecting with people who are there to learn and take the profession of sales seriously. Unlike many other conferences where people mostly just show up for the networking and the after parties, this is a conference where people show up to learn how to get better (in addition to the networking and after parties of course)

In this interview with Kyle, we go back to when we first met and talk about how we’ve grown and where we see things going in the world of sales and sales engagement. We’ve pulled out some of the highlights below, but this interview really is best watched or listened to, to really get a feel for Kyle’s passion and enthusiasm for SalesLoft, and the overall topic of sales engagement.

How We Got Connected

Several years ago, before SalesLoft was in the sales engagement category, during the live application part of our sales training, a rep used our techniques and sent an e-mail to Kyle. Kyle was so impressed with the quality of the e-mail that he wrote a blog post about it.

The rep got so excited they sent me the blog post, so I forwarded it to Kyle letting him know I trained the kid who sent it and wanted to see if his team was looking for training. He didn’t end up buying training from me, but that’s what started our relationship.

Over the years, we’ve seen eye to eye on most things, personally and professionally (other than professional sports teams), which is why I was so excited to have Kyle on the podcast, and why I’m always fired up about Rainmaker.

John Barros and Kyle Porter Rainmaker

Ability to Evolve

One reason I’ve always been a fan of Kyle is his ability to evolve. The first iteration of SalesLoft went from 0 – $7 million in a two year time and was extremely successful. But Kyle saw the writing on the wall and the limitations of the product so he effectively shut it down and rebuilt a new product and company to address a bigger challenge he saw in the industry around authentic selling and sales engagement. There aren’t too many CEOs I know that have the confidence and foresight to shut down a $7M successful business and start something new.

I’ve always believed that if you don’t constantly push yourself and evolve that you’ll get passed up and become obsolete rather quickly in today’s business world. I live my life by the Rule of 1% which is about trying to get 1% better every day. In sales, we need to focus on the day to day execution to hit our numbers but we also have to keep an eye out for the trends that are affecting our industry. We need to help our clients do the same thing. If anyone is comfortable with the status quo right now I’d be worried for them. Things are changing too fast to not have an agile mindset to business.

Living your Values and Culture

When it came time for Kyle to make the transition of the core product offering, the hardest part was getting the internal buy-in. This is where having a culture that lives their values is so important. A mini wake was held for the older products and Kyle sang Dust in The Wind.

As leaders, we need to paint the vision and then help everyone understand how they fit into that vision and what their part is. Without getting people bought into a larger vision and making them feel a part of it you’ll never get people to do more than their job and what is asked of them.

When I asked Kyle about how he lives his culture and his values, he talked about how being transparent, vulnerable, and authentic early in life gave an insurmountable amount of ROI for him, and he brought that to SalesLoft. The culture at SalesLoft is a direct reflection of that ROI on being sincere and authentic.

Kyle also wanted to create an environment where everyone could bring their talents they had been given and earned to make the world a better place and find fulfillment. It takes an incredible amount of work to make sure your team is on board with your journey and North Star. Leading a value-driven organization value isn’t complex, but it’s hard to be consistently blocking and challenging.

Using Sales Engagement to Free Up Time for Your Customers

One thing I see as I train is a generational shift. When Gen Xers like myself got into sales it was mostly a volume/numbers game. This is the mentality most of us bring to management these days. Even though we understand the importance of quality, it’s still a lot easy to ask your rep if they made their 50 dials.

Sales engagement is not marketing automation. When you’re looking for shortcuts to crush your number and smash your quota out of the water, you forget about the human part of sales. It isn’t about the ability to bombard your prospects with 85 touches a week, it’s about delivering a better sales experience. The customer doesn’t care about your process, they care about solutions for their problems.

When it comes to that level of caring, it’s very hard to do with any sort of speed or volume, which is where sales engagement tools come into play. As a rep, you can have all the machined learned intelligence on your prospects, but you’re still the one connecting. We need to think of ourselves as controlling the “last mile” before we hit “send” and making sure the content that the technology is collecting and delivering to the client has a human touch.

The Future of The Outbound SDR

Historically the SDR has been the introductory role into sales. As sales development matures and continues to leverage more tools, data, and insights to engage with clients and then analyze the results to make improvements I believe sales development will align more with marketing and operations rather than sales.

Kyle agrees that sales development is very operational, but is ultimately a function of sales, as the rep needs to make the individual tweaks to the messaging for their prospects. Kyle illustrates this with an internal example when he emailed each of his 350 employees at the end of the year.

Instead of a marketing style customization like “Hi <firstname>, I wanted to thank you for <yearsofsevice> in <department>…” he personalized each email like this. “Hi <firstname>, It was great seeing you in the hallway last Friday….” or “Hi <firstname> we haven’t had the chance to meet yet but the campaign you just launched looks amazing…”

The power of sales and sales development is in the nuance towards the end to care enough about each individual customer.

The Perfect Level of Customization

We also touched on one of my favorite blog posts from SalesLoft. It’s focused around the perfect amount of personalization. Their research of over 2 million emails, found that 20% customized was the optimal amount. The results were similar from 20%-80% personalization but then drop dramatically at 100% which I found very interesting.

Probability Chart

This reinforces how we could and should do personalization at scale. We can come up with value statements based on specific components of our solutions, personas or triggers that we can add value to and standardize on that messaging while allowing the first section to be personalized and make the human connection.

Wrapping Things Up

This truly was one of my favorite episodes of Make It Happen Mondays. It’s always great to talk with people and companies that align with your vision and values and challenge you to get better every day. Business and life are too short to associate yourself with people who you don’t enjoy working with or don’t align with your values. This is true in business, sales, and life. If you’re not passionate about what you do you’ll never be truly successful. Surround yourself with good people and it’s amazing how far you can go.

Rainmaker 2019

Rainmaker will have 1,500 of the brightest and most advanced minds in modern selling and is a crucial sales community event that’s not to be missed. Use code JBVIP to receive 50% off when registering you and your team.

A few of the speakers include:

  • Colin O’Brady – The first person to cross the entire continent of Antarctica solo, unaided and unassisted (in -60 degree whiteout blizzards)
  • Danny Meyer – The NYC restaurateur, creator of Eleven Madison Park, founder of Shake Shack, and CEO of Union Square Hospitality Group
  • John Barrows, Morgan J. Ingram, and the entire JBarrows team at the JBarrows Lounge
  • Top sales execs at Zoom, Stripe, Informatica, WeWork, Square, Yext and more

Hope to see you there! Make it Happen.

Rainmaker 2019

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