EPISODE 028: ON24’s Sam McKenna Says Showing Me You Know Me and Being the Urgent Bird Will Propel Your Sales Career

EPISODE 028: ON24’s Sam McKenna Says Showing Me You Know Me and Being the Urgent Bird Will Propel Your Sales Career

Samantha McKenna is an award-winning leader who serves as a regional vice president of sales for ON24 and has worked within the SaaS sales and marketing space for 10 years. She is a thought leader and speaks across the country on topics covering women and tech, sales, and leadership, alongside topics of domain creation, sales, and content marketing and how it all comes together to impact sales.

Samantha served four years as a board member of the Legal Marketing Association Capitol Chapter, actively volunteers with financial-literacy initiatives in Washington, D.C. and writes for publications such as Sales Hacker and Sales for Life. She holds a business degree from Florida State University and lives in Reston, VA. She originally hails from Geneva, Switzerland, is an avid wanderluster, and got her first taste of how to negotiate as she maneuvered her way through 37 speeding tickets.

Find Sam on LinkedIn!


Fred Diamond: You were introduced to us from one of our previous Sales Game Changers, Sarah Lash over at Tableau. I’ve been familiar with ON24 for a number of years, so I’m very excited to hear your journey and get some of your insights for the sales game changers. Let’s start talking about your career. Tell us what you sell today and what excites you about that.

Sam McKenna: ON24 is a marketing webinar platform. Everybody’s attended a WebEx or a GoToMeeting, something like that. They are hard to get into. You can’t see much. It doesn’t really tell you anything about your attendees when you’re in. Ours was built for marketing. It’s an engagement at scale platform that lets you take a few presenters and then spread that message out to hundreds, if not thousands, of people. What excites me about it is the way that we actually collect our data on the attendees that come in is very, very different than what you would traditionally get with a screen-sharing platform.

Fred Diamond: That’s a great resource. Let’s go back to the beginning of your career. How did you get into sales as a career?

Sam McKenna: I sort of fell into sales, and I feel like some of the most successful people in sales always say that “I kind of tumbled into this.” I was hired as an account manager about 12 years ago. When I did that I said, “Listen, I’m happy to do this job, but I’m never going to make a cold call. I’m not going to sell to people.”

The boss at that time said, “Uh-huh, uh-huh, sure, sure, sounds good,” and hired me on. After about two years I found such a fit within doing account management that my VP at that time said, “I’m going to promote you to outbound sales. I want you to bring in a new client base.” This is something where I couldn’t hide. I couldn’t figure out how to close deals based on existing clients. It was really sink or swim, and I did that within the first year. I think I broke a few records at our company in terms of sales and then the second year, same thing.

Fred Diamond: What were some of the key lessons you learned from your first few jobs that have carried with you to today?

Sam McKenna: I’m an extremely hard worker. I work long hours. I love working at night. I love coming in early in the morning. And so, what I started to think about was “how do I work smart not hard?” Then once I worked smart and not hard, “what are the results going to be like if I put those together, if I do those long hours but I’m really working smart at the same time?” I think one of the key lessons that I learned was how to apply that but then also that urgency and relationships matter.

Relationships really matter, but the urgency is key. I have a little saying: “The urgent bird gets the worm.” It’s not the early bird. It’s the urgent bird. That sense of urgency that you drive in terms of responding to your clients, in terms of getting proposals out, in terms of solving their problems. That tends to start to build a brand for who you are and what they can rely on. That was one of the most important lessons I learned in the beginning.

Fred Diamond: Urgency, that is so critical. Sam, give us a little more insight into you. Tell us what you’re an expert in. Tell us a little more about your specific area of brilliance.

Sam McKenna: I think in terms of what makes me so successful at sales, I really understand people. I have a high emotional intelligence, they say, and I think that I’m able to really understand people, their needs, their fears, their problems. I know sounds a little psychologist of me, but it’s just something that I innately get.

I think if you understand people, you understand the dynamics of their company, their teams, their challenges, what they’re measured by, how what you’re selling is going to impact them. You can really start to build a story of how you’re going to help them, how you’re going to get them to their goals. The thing that I think is important to you is you are doing something that’s going to advance them in one way or another. Don’t be afraid to have those conversations with them: “How are you measured annually? Here’s how I can help get you to your goals.”

Just understanding people and understanding relationships, how people are connected, how they connect the dots, “Do you know people within my network? Have you worked in and purchased from us before?” Understanding the dynamics of those and how to connect the dots is also really important.

Fred Diamond: Go back through your career and talk to us about an impactful sales career mentor and how they made an impact on your life.

Sam McKenna: I’ll tell you one of the first CMOs I ever worked with was a gentleman by the name of Jim Durham. Jim Durham was my first CMO who bought from me, and he agreed to meet with me. Of course I was nervous as hell. Meeting a C-suite was a big, big deal for me back then. When I met with him he was so casual. He was so smart and so helpful. One of the things that he said was “What are your goals in sales?” I said, “I really want to sell to the legal vertical. I want to get as many law firms buying us as possible.”

He said, “Why don’t you go on LinkedIn and why don’t you look through my network, find the people you want to sell to, and then just send them an email and say that we’re friends and see if they respond to you.” I kind of looked at him a little dumbfounded and said, “Are you serious?” and he said, “Yeah, sure.”

Back to the idea of “the urgent bird gets the worm,” I did that that night. I basically stayed up until four o’clock in the morning going through his network, trolling all of the people on there and then sending them emails. The thing that was so impactful was my subject line. I sent an email and I said, “Webinar inquiry from a friend of Jim Durham’s.” The response was unprecedented. How people responded because of your network, because of your relationship, because they wanted to help you even if they didn’t think that they could help you or they were the right person, they pointed you in the right direction, which was amazing.

That really gave me a lot of insights into how relationships work, what people would do for somebody they already know versus somebody who’s cold to them and also how that sense of urgency can really drive your pipeline really quickly.

Fred Diamond: Good for you for doing the follow-up.

Sam McKenna: I think this comes back to your brand. You’re going to do that and extend an offer to somebody that you trust, that you know isn’t going to tarnish your name, that you also know.

I think it’s so interesting what he said about “Go through my network and let me know who I can help you with” and that one out of 50 people you extend that to do it is the exact same experience for me. Even within our own organization, the amount of connections that I have in the D.C. area and the relationships that I’ve built can really help a lot of people. The idea of wanting to do that is always great, but then those who follow through are so rare.

However, the people who do follow through I’ll always remember. I remember who they are. I come up with an assumption about them, that’s their brand. They actually follow through on that.

Fred Diamond: Take us back to your decision on how to pursue the legal marketplace and what was that all about.

Sam McKenna: When I got promoted from account management to sales, one of the things given to me by another mentor who was actually in sales and my leader was “You can take five accounts with you so that you have a little padding, some runway of existing clients, but then beyond that we need you to bring in new customers.” What I thought was, “Okay, let me look at our customer base. Who works with us, and who spends a lot of money with us?” What I found is that we had eight law firms that worked with our company at that time, and three of them were among the top 10 law firms in the country. Three of the top 10 law firms in the country worked with us, and we were a very, very small shop back then. This was not ON24. This was my predecessor to that. And I thought “Why?” What I actually did was I went and interviewed the three CMOs from those organizations and said, “We’re small. Why do you work with us?” It came down to service, it came down to the quality of our technology. There were a few core reasons they worked with us, and I said, “I can use this, and I can expand on it.”

I really took a strategic look instead of just kind of shrugging and saying, “Let me just start working down a list” and started to make kind of a career about that. I got involved in the Legal Marketing Association, as you heard in my introduction. I started to attend meetings, get on committees, etc. I became more of a friend to people than a salesperson. I generally did want to help people, but I thought one of the easiest ways to do that was just get involved in something where people started to know my name instead of just this person who shows up to sell stuff.

The other thing that I think is interesting about that is when we started to hit the ground running in terms of saying this is who we already work with. Again, we were able to build relationships that way in a really easy manner because people wanted to be part of what other law firms were doing. I think in terms of also knowing your audience, knowing your customer, that’s also really important. People want to buy from people who know their industry, their challenges. They want to know that they’re buying from somebody who also knows their peers. I think that’s one of the most valuable things I can say. If you’re going to specialize in a vertical, really get involved with those organizations. Major, if you will, in your territory, and then minor in a vertical. Think about how you can then get involved, attend meetings, sponsor their events, etc.

Fred Diamond: What are the two biggest challenges you’re facing today as a sales leader?

Sam McKenna: When I became a leader I thought, “How am I going to do this? How am I going to get my team to behave in the same way that I do?” I know what’s made me successful; how do I scale that? I think that’s one of my biggest challenges is scaling my behavior,. My team says, “What would Sam do?” How do I scale that so that when they’re in those same situations they think and have the same trigger points?

The other thing that I think we all struggle with is pipeline. I think every single sales executive or rep can say, “I need more pipeline.” What we really try to do is focus on, again, the relationships. I can’t imagine what it was like to sell before the days of LinkedIn, which I know is our most valuable tool in terms of understanding where people come from, what they’re interested in, who they’re connected with.

But in terms of being able to build pipeline and really focusing on self-sourced pipeline so we can control it, it’s how do we drive that, how do we utilize our connections and our networks to open more doors and quicker.

I have another tagline that I use: “Show me you know me.” I’m sure, like every executive on the planet, you get 10, 12, 50 marketing emails a day from people wanting to sell you stuff. As a sales leader I love the emails that come in and tell me that I can get better I.T. reporting, which is obviously what I need. But when you flip the tables and you really have access to LinkedIn, you know everything you need to know within those first three minutes. If you can utilize that in a meaningful way, that’s really what’s going to get you in front of someone.

No, it’s not a silver bullet. Not everybody’s going to respond to you no matter how charming and “show me you know me” you are. But it’s a much easier way to do that, and I think as a core lesson I’d always say, again, that the subject line really matters.

One of the things that we do too is a lot of our customers have case studies with us. They will let us talk about them being customers. We use that in our subject line if we’re trying to reach somebody who’s worked at that company before.

Fred Diamond: “Show me you know me,” “the urgent bird gets the worm”: great sayings from our guest today, Sam McKenna. Sam, what is the number-one specific sales success or win from your career that you’re most proud of? Take us back to that moment.

Sam McKenna: I had a deal that I was working and that was basically the final deal that I needed to [achieve] President’s Club. And of course, it was the 11th hour. We’re about to sign and the CMO got cold feet, and I was like “No.” The CMO said, “You know I get it. I get what you guys are selling. I understand it. But I don’t understand why I’m going to spend so much more money on something that I just kind of think is prettier.” We were trying to get them to convert from WebEx to ON24.

And so I just thought to a basic level. One of the keys to my success is always being able to give great analogies and make somebody think about things in their own world. This was a pretty prestigious law firm, and I said, “I’m going to give you the worst example that I can really think of, but I hope it makes sense.” He said, “Okay, hit me with it.” I said, “Let’s say you’re hosting a hundred of your top partners or top clients to come to a dinner, and you have the option to serve them filet mignon, which we know is going to cost you a fortune, or you can serve them beef-flavored ramen noodle soup. They’re going to do the same thing: At the end of the day they’re going to feed people. They will likely feel full at the end, but what are they going to think of you at the end of that dinner? You’re spending a thousand X on the dinner to serve them filet instead of ramen noodle soup. Which are you going to do?“ And he said, “I’m never going to serve them ramen noodle soup.” And I’m like, “But it’s so expensive, and filet is just prettier. Who cares?” And he’s like, “I get it. Okay, we’re in.” I can’t believe that such a terrible analogy won me the deal that I needed and got me to my first President’s Club.

Fred Diamond: Did you ever question being in sales? Was there ever a moment where you thought to yourself “It’s just too hard, it’s just not for me”?

Sam McKenna: I’m a helper. I want to help people. I want to give them what they need and be there for them. That’s just the kind of person I am. I never want to inconvenience someone. When I thought about sales at the beginning I thought, I’m that girl who makes a cold call and when they say, “We don’t need you, thanks for calling,” I’m like “Okay, sorry to bother you,” and hang up.

That was my initial thought, but then I really started to think about how sales could help. If you are selling a product that you really believe in, that you know can drive value, you have the ability to make an impact to those people’s lives. You’re not a hindrance to them. You are a help to them.

I will say that sales is such a roller coaster. We all know that. It’s the highest highs and the lowest lows. You need to be resilient to make it. When you get those lowest lows you need to be able to go to bed one night or maybe two or three nights later and then wake up and think, Okay, I can get back on the horse and do this. At the end of the day, yes, it’s very, very hard, and, no, not everybody can do it. But I think that the way that you can really use your personality and use your innate characteristics to impact your success makes it so worth it [to make up] for those lows.

Fred Diamond: What is the most important thing you want to get across to junior selling professionals to help them improve their career?

Sam McKenna: I think there are two directions you can go here. Junior sales professionals either want to get into management or never want to get into management, they just want to be responsible for their territory and make lots of money forever. I would say if you are the latter and you have no sight set on management but you want to know “how do I make more money?”, “how do I get more deals closed?” the biggest piece of advice that I can give you is to never take your foot of the gas.

You will see that the most successful sales people don’t get “happy ears.” They don’t get happy ears, because no matter what, nothing is ever enough. Even if their pipeline is full, even if they’re already a 150% of their quota, they’re constantly thinking, “What’s next, what’s next, what’s next?” and at that pace. Going back to the urgency thing, it’s constantly, “How do I find more, more and more?” It’s not “Okay, great. I’ve got my few deals and I know I’m going to close this and maybe I’ll think about October and November at this point, since we’re in fall right now.” They’re always thinking more, more, more all the time.

From a managerial standpoint, if you’re thinking, “Okay, great, I’ve been successful in sales, and I’ve hit my quota, so how do I get the executive team to see me and how do I improve there?” the advice that I would give you on that side is crush your quota while you do something great on the side for your organization. Get involved in a women’s group. Get involved in marketing efforts. Build a program that’s never been built at your company that you think you can do to improve your company. Do that while you crush and exceed your quota.

At the end of the day, the only thing you are paid to do from a sales perspective is to hit your number. Nothing else matters. If you’re at 70% of your number and you’re doing some great mentorship on the side, that’s lovely and all. Hit 100% of your number, that’s what’s most important. If you can do that or hit 120%, 130% of your number and build something else, you’ll nail it. I think that’s exactly what I did at ON24.

Fred Diamond: Very powerful. What are some of the things you do to stay fresh? What are some of the things that you do to sharpen your saw?

Sam McKenna: I think the most important thing you could do is read. I know that seems really, really basic, but I try to keep an hour of my day at either the front or the back end where I’m focusing on reading and I can really focus on articles, what’s happening in the news, what’s happening on TechCrunch for us. I really need to understand what’s happening with our clients and what’s happening on the daily to understand that.

I also read a lot of business books. I’m a junkie in terms of that, so I’m always really interested. I just started a new book called Principles, which is being heralded as one of the biggest improvers for people like Bill Gates and Arianna Huffington. I think the other thing too is sign up for publications like The Daily Skimm, which I love. It’s just a quick rundown of everything that I can read in bed before the morning. I look at Fortune’s articles as well every single day that I think are important. Just stay ahead of what’s going on.

Be knowledgeable, and not just about what’s happening in your industry but others. Do you know what’s happening in politics? Do you understand what’s happening within professional services? Have your arms around that.

Fred Diamond: And also, of course, with your customer, what is going on big in their industry. Sam McKenna, what’s a major initiative you’re working on today to ensure your continued success?

Sam McKenna: I am trying to scale the speed at which we find pipeline. Again, I know that seems basic, but one thing that I’m really working on is how do we leverage our connections  and how do we leverage people who have purchased from us before to speed up the deals that we’re working on now. I’ll give you a great example.

End of the quarter last week, we closed a pretty monumental deal that we’ve been working on since January. When we were closing, close to closing that deal, our decision maker said, “We’re ready to go, but my CMO is going to need to sign off on it.” We’d never even looked at the CMO, which I’m disappointed that we didn’t even look at our network there. But we come to find out the CMO knows somebody high on our executive team very well. Our executive reached out and said, “Hey, we’re working on a deal” and the CMO came back and said, “I’m very familiar with ON24. I was your purchaser before at my previous company.”

We found his previous company. We’d seen that he’d been at his current company for two and a half years. What a miss for us, right? We could have had that business at the end of 2015 instead of the end of 2017. I’m trying to figure out how to scale those connections, how to find those faster, how to make sure we don’t miss those things so that we can get that revenue two years in advance versus now.

Fred Diamond: You mentioned The Challenger Sale before, and we haven’t really spoken too much about it. But it comes up not infrequently. The Challenger Customer came out recently, and I believe they said that the number of customers in an enterprise deal that you need to interact with was like 5.4. I’m good friends with Brent Adamson, the co-author of The Challenger Sale and The Challenger Customer, and I believe he said that number’s even increased to six.

Sam McKenna: I adopted The Challenger Sale, after I heard my solutions engineers do this years ago. I was always so keen to look at our clients, our prospects who say, “This is how we do it” and for me to say, “We can do it that exact same way. Just come over here instead.” When I was junior in sales and one of my solutions engineers was on the phone with a prospect and they said, “This is how we want to do it,” he said, “Why?” And I said, “Oh, my God.” I was so nervous that the client was going to push back and say, “Well, that’s the way we’ve always done it and just do it this way, or we won’t be able to.” I listened to this conversation. I listened to how he challenged them. He said, “Well, have you thought about this or have you thought about that?” My fear was that nobody wants to change. Everybody hates change, right? Most everybody hates change. And so, if we suggested you can come over here and change your process, they’d never do it. Man, was I wrong.

I think if you really have a look at the way that your client is doing it [you can] then say, “We can do that, but have you thought about this or look at the success of that.” Start to challenge the way that they think, challenge the way they sell, they market, whatever it is you need them to do to use your product. Get them to open their mind a little bit. They might say, “No, we want to do it this way.” But by doing that challenger piece you’re also showing your level of intelligence and your aptitude for what they’re doing. You understand their business. You understand what they need to do in order to be successful, and they’ll welcome that versus somebody who’s just saying, “Sure, square peg, square box, let’s do it.”

Fred Diamond: Sam, sales is hard. People don’t return your calls or your emails. Why have you continued? What is it about sales as a career that keeps you going?

Sam McKenna: I remember my job before I got into sales. I worked in a marketing capacity, communications capacity. I had my salary, and I knew what I was going to make every single month, and that was it. No matter if I was the top-tier talent on that team or not, that’s what I was going to make. When I got into sales, I even remember my first commission check as an account manager. It was $900, and I about fell out of my chair back then.

I thought it was so amazing and exciting and that, surely, somebody had made an error. But that instant gratification of knowing that your effort, your character, your intelligence, who you are can pay off financially was so interesting to me. I’m extremely competitive as well, which I think you really need to always be to be successful in sales. I used to be a ranked tennis player, very, very competitive in terms of my achievements, and that also pays off in sales.

You have a year-long race to get somewhere. I think, again, the lows can be superlow. You work on a deal for nine months, and you find out you lose to somebody, or the CMO leaves and you have to start over. Those are devastating blows. But there are always great deals around the corner, and the financial payoff that can come with it is tremendous.

Fred Diamond: Why don’t you give us one final thought to inspire the sales game changers listening to today’s podcast?

Sam McKenna: My biggest thing to you would be to build your personal brand. Think about who you want to be and when people recommend you what are they going to say about you. That should be your brand.

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