Kyle Porter, who founded and led Salesloft for the past dozen years, stepped down from the CEO role and was named Salesloft’s Chairman last week.  In his place, the firm named SaaS veteran David Obrand its new CEO.  Obrand is also joining Salesloft’s board.

Porter grew Salesloft into a unicorn with a $2.3 billion valuation.  In December 2021, Vista Equity Partners took a controlling interest in Salesloft. 

Over the past six years, the company grew ARR 20-fold and now supports 4,500 customers.  It also began its international expansion with offices in London and Singapore.

The firm began as a contact email enrichment service based on email guessing but expanded its vision to Sales Engagement with the launch of its Cadence service.  It continues to widen its scope, with the addition of modules for Deals and Conversations.  Functionality includes sales engagement, conversational sales, meeting scheduling, a partner ecosystem, and forecasting.  Its Rhythm service, which dynamically provides prioritizes a sales rep’s day, was announced at its August Saleslove conference.

I’ve known Kyle Porter for around a decade. I was impressed when he mothballed his first email guessing product because it wasn’t aligned with his belief in sales authenticity. It was a gutsy move. While he didn’t burn his boats (i.e., immediately remove the product from the market), he stopped selling the service and phased out the product while fulfilling current contracts.

Porter is also a gifted storyteller, which he emphasizes as a skill that sales reps should hone.  His personal story is embedded into his management style.

I had the opportunity to interview Kyle on Friday. The conversation below was edited for length.

Why have you chosen to move upstairs?

There are two major reasons.  The first is for the greater good of the business.  I’ve seen this market unfold and the opportunity that we have in front of us just open up.  It’s unlimited what we can do in sales and revenue generation.  And our mission has always been to fundamentally change the profession of sales forever and really build a world where sellers are loved by the buyers they serve.  I want every Lofter to have our mission as their primary focus within this business.  And that means I need to have it as well.  My goal is to always do that.  And when I looked out to the future of everything that we could achieve, the biggest fear I had was that I wouldn’t be the right person to help us get there – that I would leave something on the table.  

My skills are always growing, always developing.  I consider myself a lifelong learner.  And I’ve worked really hard to be just as good as I can at this stage as I was when there were zero people at the company. That evolution, however, is hard work.  And that self-development is a deep investment.

The second piece of this is more of a personal perspective.  On my very first date with my now wife…she asked me what my dream was, and I told her it was to run a technology company that makes a dent in the universe.  I asked her hers, and she said it was to restore the glory that was the Florida citrus industry…

Now with someone like David, he’s already gained that wisdom, experience, know-how, and recall.  It’s so natural for him.  And I felt like we could accelerate the development of the CEO’s capability to take us to the next level by bringing in someone like David.  So really, it’s based on my limitations as CEO.  The opportunity ahead of us is just so big.  And we have an amazing future in this business.  We do the right things, and we serve our customers with excellence.  There’s no limit to what we can achieve, so I wanted to accelerate the office of the CEO’s capabilities and really improve the handicapped chances to achieve our mission. 

Some opportunities came up to really achieve that mission that she’s been on.  And I realized that my talents and resources could greatly assist her just as she sat on the sidelines and helped me achieve my mission for over twelve years.  I realized that it’s not right for this organization with so much growth ahead to have a CEO that’s not singularly focused on the mission of the business…I’m going to do tangerines with my wife, and that meant that it was the best decision to have someone that would be singularly focused on the mission of this business…

Of course, there are also my three children. While my daughter Brooklyn (8) is still going through the change curve of me no longer being CEO, I’m incredibly excited to pour more time and attention into her, my son Clark (5), and daughter Abby (1) as well!

How active will you be as the chairman?

Pretty active.  We have a founder lunch that I’m going to continue.  I’ve been corresponding with many customers this week, and I will retain those relationships and meet with them continuously.  I’ll be a board member.  David has asked for a once-a-week meeting indefinitely with him.

I just have really deep relationships with so many people inside the organization and with so many of our customers and partners.  My enjoyment and my passion are to continue to work with those people.  So customer meetings, board meetings, and one-on-ones with the CEO.

We got some really fun content projects that we’re working on.  We’re going to be doing some work together to really show the market what’s happening and what’s changed and how to be more effective in this new world of modern sales.

What were the top criteria for selecting your successor?

Number one is that they are aligned with the mission of the business.  When we talk about fundamentally transforming sales and revenue forever, this person that we brought on board had to have that in their heart already.  Number two is they have to realize and understand that organizational health is the biggest sustainable differentiating advantage that any company can have.  So when we love on our Lofters, they turn around and love on our customers, and the CEO needed to understand those dynamics and be willing to continue running this business with that framework and mindset.  Three, I wanted someone that was well-rounded functionally.  Not just a sales leader, but someone that understood product engineering, finance, marketing, [and] customer success.

I saw it firsthand when David Obrand got up and spoke with the product and engineering team.  I sat, and I listened to someone say things that I wish I had thought of saying to them in the past.  Things that I didn’t know and didn’t experience.  And the way he connected with them was on a very deep level.  And it was really refreshing for them to see someone that understands them even better than I did.  So that was really cool.

When you think about succession as a founder, there’s a point at which your skillset, knowledge, or experience isn’t the right fit for taking the company to the next level.  And many executives, out of hubris, choose to continue in that role, even though they may not be the best person for that role.

I believe exactly what you said.  But I also believe that we really don’t have any limits except for those imposed upon us by ourselves.  I’ve always believed that we can grow and develop into that next stage, and I’ve always believed that for myself, but that investment sometimes takes time.  And if you have other things that you’re focused on, it’s more difficult to get down that development path.

You had a quiet layoff last week.  Usually, you’re more transparent about these things.  Why the shift away from the prior transparency, and why was it necessary to do so?

Necessary is an interesting word.  I teach our leadership team that they don’t need to do anything; they always choose to do certain things.

On the transparency front, we did have a layoff after COVID.  And we didn’t make a public announcement on that, as well.  We believe that’s a private thing for the people that are part of the organization.  We want to be super transparent internally about everything that happened.  And if someone goes out and posts something, we don’t stop them or send them a note saying, don’t write that by any means.  But that is a private kind of situation for the people who are impacted and affected.

Now, I am certainly helping people to find jobs.  And we’ve assembled a list.  And I’ve made many introductions.  I’ve brought a lot of investors in, And we are helping those folks to find their next path.

SalesLoft, like many companies, saw lots of growth in the market and then saw some headwinds in front of us.  And the way we think about it is that you’re in an airplane, and when the headwinds come, you can do two things: you can accelerate through and burn all your fuel, or you can lay back a little bit, let the headwinds pass, and pick back up.  The decision we made was to lay back a little bit, let the headwinds pass, and then pick back up with the business.

What advice would you give founders of technology startups?

Really obsessing over the problem you solve is the first and foremost most critical thing that founders need to do.  And when I say obsessed, I mean you need to get everybody in the organization on board with caring so much that they love their customer; they love solving the pains for them.  And the company that cares the most is the one that’s going to win.  Number one is that customer obsession and a really deep focus on the problem that you solve to the point where it becomes just a daily rhythm of your life.

The second one is aligning your organization to go after your mission.  The mission statement is something where you’re one stop short of changing the world.  We want to fundamentally transform sales forever.  And that’s what we’re here to do.  And so we need to hire people who believe in that mission, even down to the engineer.

We’ve created this whole community of people from every walk of life who love sellers and who understand the beauty of what sales is and how it transforms economies and markets.  How it helps companies hire, invent, bring new products to life, and really change the fabric of our society.  Making sure that your team is focused on that mission is critical.  Then you got to have the rhythms in place where they’re being held accountable [and] where you’re achieving your goals.

You’ve emphasized the importance of culture.  How did Salesloft benefit from your five core values?

What we’re looking for when we hire people is not that they’re five out of five A+, but that they have many of the core values [and] also believe that the other ones that maybe they’re not as strong in are important enough to work towards.

The other thing is that core values are a way to stop yourself before you make a mistake.  Once a mentor told me [that] a good leader makes a mistake and quickly fixes it, [but] a great leader is about to make a mistake and fixes it before they do.  And for me, that’s what the core values are.  If we say that we want to be glass half-full, and I find myself about to say something negative.  In the old days, I would say it, learn it, and fix it.  But now, before it even comes out of my mouth, my head says, “glass half-full,” and I change the way I deliver that message.

Or if I’ve got a decision where I can go left, and it’s maybe better for money and then go right, and it’s better for customer experience.  Then, customer obsession comes into my mind before I make that decision so that I can go right for the customer.  We look at core values as triggering mnemonic messages in your head that help you to be the person you want to be.

As a CEO, you’ve got to repeat those [values] over and over again.  Reward people who exhibit it.  You’ve got to praise those who showcase it.  Repetition is persuasion in that regard.

What is one mistake you wish you could have avoided?

We never anticipated the market would come back so fast post-COVID.  Nobody did.  Had I understood that, we wouldn’t have slowed down like we did.  But then, we also never anticipated that the SaaS market would crash the way that it did.  Had we understood that, we would have slowed down a little bit more before we did.  Hindsight is 20/20.  If you can predict those things, you can be a multi-billion-dollar hedge fund manager. 

We’re always trying to align market demand with the resource supply of the organization.  So that’s a continual trade-off that we’re working to make.

Are you looking forward to more time on the citrus farm?

I’m really excited.  One of the things we do is send tangerines out to our customers.  Every single year we do it, and I’m not going to miss that.  We’ve got to keep producing great tangerines, so we can keep getting them into the hands of our customers. It is a joy and a passion of mine and my wife’s.  She’s been so helpful to me on this journey, and I’m excited to help her follow her dreams.

Any last thoughts?

Yeah, we’re in a great spot.  As a company, even with what we’ve seen in the downturn in the marketplace, we saw a really strong end to our Q4, and Q1 is off to a great start.  Our CEO is highly capable.  He’s wise.  He’s been welcomed with a huge Salesloft hug inside the organization, and I’ve seen our customers and market participants really appreciate who he is and what he’s going to do.  We’ve got a big opportunity to fundamentally transform the sales profession ahead of us.  And we’re going to do it.

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Resources

• Salesloft Website
• Salesloft Products
  • Cadence
  • Deals
  • Conversations
• Kyle Porter’s LinkedIn Profile