This week on the Sales Hacker podcast, we speak with Ryan Lallier, Director of Inside Sales at InsightSquared.
Ryan has a diverse background in Sales, with positions ranging from individual contributor to head of sales roles at companies like Dataminr, Gartner, and YayPay. Ryan is also a member of the Revenue Collective, and founder of SalesGevity, and advisory and consultancy for start-ups.
If you missed episode 73, check it out here: PODCAST 73: What do Venture Capitalists Want w/ Semil Shah
What You’ll Learn
- About Ryan Lallier and InsightSquared
- Ryan’s Sales Career Journey
- Picking the Right Company to Work For
- If You’re a Sales Leader, Recruitment Is One of Your Primary Jobs
- Personalization in Prospecting
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Show Agenda and Timestamps
- Show Introduction [0:00]
- About Ryan Lallier and InsightSquared [2:00]
- Ryan’s Sales Career Journey [6:53]
- Picking the Right Company to Work For [19:35]
- If You’re a Sales Leader, Recruitment Is One of Your Primary Jobs [23:39]
- Personalization in Prospecting [26:58]
- Sam’s Corner [46:44]
Show Introduction
Sam Jacobs: Hey, everybody. It’s Sam Jacobs. Welcome back to the Sales Hacker Podcast. We’ve got a great show with a good friend of mine today, Ryan Lallier who is a director of inside sales at InsightSquared. He’s currently an individual contributor, and he’s been a VP in the past. He’s moved back and forth between leading teams and also being an individual contributor. That trajectory gives him a lot of empathy in terms of how he works with and serves the VP of sales and the VP of marketing.
First, we want to thank our sponsors. We’ve got Lucidchart Sales Solutions. Lucidchart is the leading account planning platform for modern sales orgs. With Lucidchart, you can visually map out key contacts and crucial account data to uncover critical insights that will allow you to close bigger deals faster.
Our second sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.
Now, without further ado, let’s listen to this interview with Ryan Lallier.
About Ryan Lallier and InsightSquared
Sam Jacobs: We are incredibly excited to have a good friend, a member of the Revenue Collective, but also a longtime VP of sales in the Northeast, in the Boston and New York city areas, and somebody that has a really interesting career journey to tell us about it. I’m talking about my friend Ryan Lallier. Ryan’s currently Director of Enterprise Sales in New York and New Jersey for InsightSquared. But before that he was the VP of sales at an early stage company called YayPay. He was the VP of sales at a place called Dataminr, which is a unicorn in terms of valuation. He was a VP of inside sales at Jibe. He’s also been an individual contributor at Gartner. So he’s moved around, and he’s been both an individual contributor and led teams of people. And he’s also just somebody that’s incredibly passionate about sales. He runs his own Podcast called Demo, like a user. The first thing that we like to do is we like to hear your baseball card.
Ryan Lallier: I work for a company that’s headquartered in Boston called InsightSquared; we are a business intelligence platform. We help sales and marketing leaders see things more clearly in terms of overall metrics, health of the business forecasting, and pipeline management. I haven’t been there for too long, but enjoying the ride so far. We have a great executive leadership team and a phenomenal product.
Ryan’s Sales Career Journey
Sam Jacobs: What’s your background? How long you’ve been doing sales?
Ryan Lallier: I’ve been in sales since 2000. I responded to an ad for a company called Connecticut Telephone. It was my first sales job. I didn’t realize that wearing a suit jacket was the appropriate move. So when the VP of sales said to me, “Why aren’t you wearing a jacket?” I looked at him dead in the face and said, “Quite frankly, I can’t afford one.” He was like, “Okay, I have good news for you. If we hire you, we’re going to give you a $1,500 credit to Men’s Warehouse.”
I did that for a year and a half, and I made friends with some really awesome guys. And this one guy, Greg, ended up leaving Connecticut Telephone to move to Boston to become a stock broker. He would call me at my desk every Monday and say, “It’s time to leave Connecticut. You must come to Boston. We’re having a blast here. There’s tons of opportunity.” And I kept blowing him off. But then one morning I woke up, and I said, “You know what? I’m tired of doing this Connecticut Telephone gig. I want to challenge myself and do some something new.” I walked in, quit my job, and the next day I packed my car and drove to Boston. I called Greg on his cell phone and said, “Hey, I’m downstairs, let me in.”
I eventually landed an inside sales job for this UK expansion company. They loved the fact that I quit my job, packed up my broken car, and drove to Boston with very little money. They hired me right on the spot. I closed logos like Bank of America, for example. Closing a $55,000 deal over the phone when you’re pretty young and just cracking into your sales career is a pretty cool accomplishment.
After 12 or 13 years, I landed at a company called ThinkingPhones, where I got my first inside sales manager job, managing the West team, handling all the SDRs and the AEs. At one point, this guy Michael O’Dell came over to me and said, “Hey, I’m going to be leaving the company soon. Would you come with me? I need someone like you who can come in and really immerse themselves into the business, get the SDR program up and running, create organic demand, get the AEs buttoned up, put processes in place, teach people how to run a discovery call, teach people how to do a demo, how to close deals, inject sales methodology into the culture. Will you do that for me?”
So, I moved to Manhattan to work with Michael. Fast forward to today, and I’m still in New York. I was a sales leader a few times here. As you mentioned, for Dataminr, I built the inside sales team from zero to 16 people, (and several million dollars in ARR), and put that whole program in place. I also spent some time with Gartner. I was also the VP of sales at YayPay. And now I’m with InsightSquared out of Boston.
Picking the Right Company to Work For
Sam Jacobs: Do you miss being a VP? How do you reflect on that experience?
Ryan Lallier: If I’m being frank, I don’t miss working for founders, especially those who are not serial founders. First-time founders go through their first two or three VPs quite rapidly. They don’t hold on to that individual long enough to really see it through and give that a person opportunity to flourish, where a seasoned entrepreneur would understand that it’s going to take my VP at least nine months to get up and running.
RELATED: The Secret To Sales Success – Sell What You Love
If You’re a Sales Leader, Recruitment Is One of Your Primary Jobs
Sam Jacobs: I know a lot of people that have really loved working for you. When you think about what it takes to be a great leader or manager, what are the things that emerge for you?
Ryan Lallier: I’m a strong believer that the sales leader has to be the best recruiter in the business. So when I landed at Dataminr, for example, I went over to the recruiting team and I said, “Can I please have a LinkedIn recruiter license? I want to have my own set up for recruiting on LinkedIn.” That allowed me to go in and build my list. So if the SDRs that were at other companies that I wanted to try to pull them out of, I got to build my list of AEs with backgrounds that I knew would be a good fit for Dataminr. I built templates and cadences, and just got that whole recruiting engine almost automated.
I was able to reach out to people and say, “I love your background. I love what you’re doing. Can we talk? Even if you’re passive and not looking to make a move, that’s great, but let’s start the relationship now because I’m planning on being here for a long time.” So I did that as step one and that really just allowed me to build my own pipeline. You can’t rely on others all the time. You have to really start to build out your own pipe pipeline there.
Personalization in Prospecting
Sam Jacobs: What do you think people are doing wrong when it comes to actually being great at sales?
Ryan Lallier: Where I see a lot of salespeople fail, is they think it’s an activity-based sport: “The more touches, the more I’ve increased my chances. That might be true. But as you level up in your career, and you sell into larger deals, I could tell you that, a CMO or CFO or any C-level executive in a $3 billion publicly traded company does not want to be on your 13, 14, or 15-step cadence. They’re going to tune you out, and they’re not going to see your emails anymore.
Do your research, and understand the business. There’s so much information at your fingertips now, that it’s disrespectful to not take the time to research the company and reach out with an intelligent message and a reason to talk. Sam’s Corner
Sam Jacobs: 45:07 Hey folks it’s Sam Jacobs. It’s Sam’s corner. I really, really like that conversation with Ryan. You can hear. He comes from a completely blue collar background. His guidance counselor told him not to go to college, which you know, I guess I’m sure, I read a lot of VCs out there like a lot of super rich white people are telling everybody else that college may not be the best. Maybe that’s true, maybe it’s not. But all of those people that give that advice typically did go to college. So we’ve got to look at how they voted with their feet in addition to their sanctimonious advice.
Sam’s Corner
Sam Jacobs: Hey folks, It’s Sam’s corner. There was a lot of great lessons on this episode. One of them is really about picking the right company, right?
Ryan mentioned that the serial entrepreneur founder often has more confidence than a first-time founder, and the first-time founder sometimes just don’t have the patience that’s required to really execute a game plan.
The second thing we were talking about is this level of personalization when it comes to outreach and making sure that when you’re reaching out to people, you’re taking the time to understand their context, to understand their background, and to do a little bit of research.
One last thing: if you’re a VP of sales, if you’re a leader, if you’re a sales manager, if you’re responsible for a group of people: One of your number one job is recruiting.
What We Learned
- About Ryan Lallier and InsightSquared
- Ryan’s Sales Career Journey
- Picking the Right Company to Work For
- If You’re a Sales Leader, Recruitment Is One of Your Primary Jobs
- Personalization in Prospecting
Don’t miss episode 75
Before we go, let’s thank our sponsors. Outreach, the leading sales engagement platform and Lucidchart Sales Solution, which is the leading account planning platform for modern sales orgs.
If you want to reach out to me with feedback, you can reach me on LinkedIn. If you haven’t rated the show, please give us five stars on the iTunes rating system so that we can remain in business and continue to bring you this show.
As always, thanks so much for listening, I’ll talk to you next time.
