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Steve Whittington is the President of Roadmap Agency, a firm dedicated to driving business results for small to medium enterprises. With a deep background as a “recovering executive” and private consultant, he focuses on helping companies achieve at least 2x growth. Steve is the agency’s driving force, specializing in a comprehensive approach that includes strategy, brand development, demand generation, sales, and customer retention. He is also the CEO of BoomBright Media, a startup that is bringing leading-edge digital display signage to the marketplace combined with creative services to develop unique immersive brand experiences. Steve is the author of Thriving In The Customer Age.

tune in

Here’s a glimpse of what you’ll learn:

  • [0:22] How Steve Whittington runs the Roadmap Agency, focusing on clients seeking growth
  • [3:28] The fusion of two smaller agencies to provide a full suite of tools for the market
  • [4:49] The importance of drafting a memorandum of understanding before a business merger
  • [8:30] Steve talks about the role of an executive coach in facilitating team dynamics post-merger
  • [15:59] Roadmap Agency’s approach to identifying a client’s real needs beyond their initial request
  • [20:23] BoomBright Media’s journey, from trial to successful launch
  • [26:22] Common mistakes in the sales process that companies often overlook
  • [32:13] Steve shares Roadmap’s client success stories
  • [34:57] How Steve entered the agency world dating back to the dotcom era
  • [37:16] The significant role emotional intelligence plays in corporate executive leadership

In this episode…

Are you struggling to scale your business effectively? What if there was a method to streamline your brand, sales, and marketing strategies simultaneously? Are you wondering how to align your organization for long-term success?

Growth expert Steve Whittington delves into the transformative world of strategic business growth. He shares invaluable insights from his dual roles as President of Roadmap Agency and CEO of BoomBright Media, detailing how they meticulously navigated the merger of two agencies to create a unified, results-driven organization. He also underscores the necessity of emotional intelligence in leadership, the art of strategic patience, and the immense potential of integrating AI into sales processes.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Steve Whittington, President of Roadmap Agency, about scaling business initiatives and refining the sales process. Steve explains how he runs the Roadmap, the fusion of two smaller agencies to meet the vision of providing a full suite of tools for the market, Roadmap’s approach to identifying a client’s real needs beyond their initial request, and BoomBright Media’s journey from trial to successful launch.

Resources mentioned in this episode:

Special Mention(s):

Related episode(s):

Quotable Moments:

  • “Anything worth doing is not easy, but to be truly unified, a merger is essential.”
  • “We drive initiatives, not projects.”
  • “It’s not just about getting the result — it’s about how you make other people feel along the way to get the results.”
  • “AI isn’t just about saving time, it’s about gaining insights you might have overlooked.”
  • “We didn’t get lucky. We were prepared for luck, and we let the market decide.”

Action Steps:

  1. Define and document your sales process stages, including how deals progress from one stage to another: Instituting a clear sales process ensures consistency and helps identify areas for improvement, addressing common gaps.
  2. Regularly seek executive coaching to enhance leadership and foster effective team collaboration: Coaching can significantly improve emotional intelligence, leading to better workplace relationships and productivity.
  3. Integrate AI into your sales workflow for note-taking, profiling, and analyzing conversations: Steve discussed how AI can save time and provide deeper insights into clients’ needs, thereby streamlining the sales process.
  4. Implement a CRM system to improve lead tracking and customer interaction management: As mentioned in the episode, a CRM system enhances accountability and follows up, vital for sales success.
  5. Engage with thought leaders on platforms like LinkedIn to broaden your knowledge and perspective: Steve advocated for leveraging social media interactions for continuous learning and idea generation, vital for staying competitive.

Sponsor for this episode

At Rise25, we’re committed to helping you connect with your Dream 100 referral partners, clients, and strategic partners through our done-for-you podcast solution.

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We’ll distribute each episode across more than 11 unique channels, including iTunes, Spotify, and Google Podcasts. We’ll also create copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90xAtariEinstein BagelsMattelRx BarsYPOEOLending TreeFreshdesk, and many more.

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.

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Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

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Episode Transcript

Intro 0:01

You are listening to Inspired Insider with your host, Dr Jeremy Weisz.

Jeremy Weisz 0:22

Dr Jeremy Weisz here, founder of inspiredinsider com, where I talk with inspirational entrepreneurs and leaders today, is no different. I have Steve Whittington. And Steve runs the Roadmap Agency. You can find that Steve, before I formally introduce you, I always like to point out other episodes of the podcast People should check out. Two fan favorites. This is a part of the top agency series. I had Adi Klevit on. She’s got an interesting niche. See if she is kind of an easy button for a company to create SOPs, so she comes in and helps them with it could be Client Onboarding. Could be staff onboarding could be whatever they need to smooth out in their processes, and she’ll come in documented and help them do that. And so check out that episode I did with Adi Klevit.

Also, we just geeked out on our favorite productivity tools, really, in our tech stack. So that was a good one. Another one was Todd Taskey. He helps pair agencies with private equity. So he helps sell agencies. He’s got the Second Bite Podcast because he found that sometimes, with the private equity situation, these agencies will sell make more on the second bite than they do on the first because private equity sells again. So that’s an interesting episode in the landscape of agencies valuations and everything like that. So check that one out.

This episode is brought to you by Rise25. At Rise25 we help businesses give to and connect their dream relationships. And how do we do that? We actually do that by helping you run your podcast. We’re an easy button for a company to launch and run a podcast. We do the strategy, the accountability and the full execution. Steve, we call ourselves the magic elves that run around in the background and make it look easy for the host of the company so they can create great content, create amazing relationships, and, most importantly, run their business. For me, the number one thing in my life is relationships. I’m always looking at ways to give to my best relationships. I found no better way, over the past decade, to profile the people in companies I most admire and share with the world what they’re working on. So if you’ve thought about podcasts, you definitely should. If you have questions, go to or email us at [email protected].

I’m excited to introduce Steve Whittington. He’s president of Roadmap Agency, and they’re dedicated to driving business results. And we’ll talk about some of the things he sees clients struggling with. He focuses and the company focuses on clients who are stuck but want at least 2x growth. Their approach is really all encompassing. So they start with strategy and brand. They go into demand, generation to sales and customer retention, and really they look at everything that’s needed in that process. It could be web development, systems, CRM, sales, collaterals, playbooks, anything that will help make that happen. He’s also CEO of BoomBright Media that was actually incubated inside of Roadmap Agency, which is interesting, and we’ll talk about that as well. So Steve, thanks for joining me.

Steve Whittington 3:21

Happy to be here.

Jeremy Weisz 3:23

So just start off and tell us more about Roadmap and what you do.

Steve Whittington 3:28

For sure. So Roadmap was formed from two smaller agencies that were merged together to be able to meet the vision that the partners had, which was to support small to medium enterprises with a suite of tools that they need to go to the market successfully. What we saw in the marketplace was a lot of specialization happening so somebody that would run SEO or paid ads or just build websites. And the truth of it was, is that a lot of the smaller companies or medium-sized companies don’t need the very deep, deep niche specialty.

What they need is somebody that can look at everything and bring it all together to drive results. So Roadmap was formed with that intent in mind, from a brand agency and a web development and digital agency, and then my background, I was doing private consulting, and I call myself a recovering executive, and we pulled all that together to create a suite of capabilities that can support that group of clients.

Jeremy Weisz 4:29

Talk about why merge, as opposed to referring back and forth. Merging is probably a lot of time, energy and stress, I imagine, but I’m sure there’s advantages to it as well. So what was the decision to merge, as opposed to, hey, let’s just refer back and forth and have a close-knit relationship.

Steve Whittington 4:49

The truth is, we started that way to determine if there was going to be a fit with the partners, and so we were referring back and forth. But that can be disjointed. You don’t have the same culture, you don’t have the same processes. And so if you really, really want to go to market in a unified way, you need to come together and agree to that. And that is more difficult, that is more challenging. But anything worth doing is not easy, but to your point, we trialed it out by doing referrals back and forth for about 12 months prior to actually merging.

Jeremy Weisz 5:28

Let’s say someone’s listening to this and like this sounds really interesting. We have a really tight-knit partner that we’re always referring back and forth, and we’re considering maybe we’ve never even thought of doing a merge, or merging, what’s a couple learnings from navigating that merger that you could share?

Steve Whittington 5:49

The first thing is to capture all the intents of the various new partners with a memorandum of understanding before you even get to a letter of intent, or actually making it legal. So doing that first is get all, and that’s professional and legal and personal aspirations. So some people might look at merging with another entity as an ability to actually take some workload off them. So they’re going to expect somebody that say that’s better in business development to take that workload off them. So you have to get all that out on paper first, and that takes a while, and get everybody to agree to that. And then you’ve got, of course, the valuations and that stuff that has to be sorted through and that can be tricky and challenging and emotional.

You got to sort through all that stuff. And there might be some cash injections from various partners to pop things up and whatnot. So, there’s a pile of that, a lot of moving pieces, right? And so that takes some time, okay? So once you’ve decided that you’re going to be together, my next recommendation was get yourself an executive coach that holds the entire team together and learning how to work together for at least the first year, and we had the insight to do that because of some previous experiences we’ve had. And so we had that. And so we all had this executive coach that held us accountable and then worked with us on a one-to-one basis to make sure that we could gel the team. We did that for two years to really form a strong partnership, even though, quite frankly, the partners had known each other.

All had known each other for in excess of 10 years, until you’re working together, until you’re in a very tight relationship together, it’s a different story. So getting that outside perspective, to hold different people accountable and have another lens on things, and allow you to back away and be objective is critical, because there’s a lot of emotions involved when you have people that have independent businesses and that are now part of something bigger, that you know somebody is now, quote, their boss, that they’re accountable to, and they never used to be that way. So you have to consider all…

Jeremy Weisz 7:57

They were independent, and they’d have to answer anyone.

Steve Whittington 8:00

That’s right, yeah, yeah. Like a solo entrepreneur with, like, just contractors, which is, a lot of smaller agencies are that right? One subject matter expert with a team of contractors. Yeah, it’s a different world, right?

Jeremy Weisz 8:15

Talk about, how do you choose a coach? And I love to hear, how did they run the coaching sessions? Is the whole leadership team there. Do they do individual? Start off with, how did you even go about choosing a coach? It’s obviously a really important decision, because they’re going to help lead the team a little bit.

Steve Whittington 8:30

Yeah, for sure, like, well, Ernest, barbaric was the chap that we worked with, and great, great guy. I had known him for a while, but again, the other team members needed to feel comfortable, and so they had to interview him and talk with him and all that kind of stuff. So we had a bunch of options. Because I believe in coaching. I’ve had tons of coaches throughout my life and mentors and been that for other folks. So, I take the medicine and I give it out, and so I believe in it. So we interviewed a number of coaches to see what was a good fit for the team, and Ernest ended up being a fit for the team, and he has for what we needed.

We didn’t need someone to drive business results. We needed somebody with incredibly high emotional intelligence to be able to look at the various different partners and extract and support us in the different ways that we needed to be supported, and then figure out how to bring us together as one unit. Now he did a wonderful job of that and had the skill set to be able to navigate those waters. So I wasn’t looking for somebody to help me read a PNL or to create a strategy and initiatives and rocks on my EOS system. I was looking for somebody to help us as a form, as a partnership team, and so have the emotional intelligence, which I lacked and needed. And he did that job wonderfully, and still works with us to this date.

Jeremy Weisz 8:31

How were the sessions run? Did he start off with individual and then do a group, or? Yeah, and then, do you remember any breakthroughs in particular that you could share from early on, when you’re first, like you said, sometimes emotions are high with their companies, and there’s a lot of moving pieces. What was a breakthrough that you had from working with earnest?

Steve Whittington 10:34

Well, in particular when we did the disc profiles and we learned, and that was up front, and we learned how all of us like to communicate, and how we communicate, and what’s important to us. And so seeing those differences, and some of polar opposites, right? And then having that understanding as to how we show up and how we hear each other, and the types of things that pushing a partner in a certain way that doesn’t work for them, like they just their personality profile is they’ll never be that, right? And so then being able to see that and understand it and go, okay, well, let’s have you focus play to your strengths, as opposed to trying to get you to play to some place that you’re just not strong.

So acceptance of that, but he was just really good at coaching us through those mechanisms. But that was one of the big things early on, is really starting to understand our different strengths and weaknesses and how we communicate, and types of communication styles. As you can tell, I’m very direct, a bit of a bull, right? And you have a partner that is more like, likes to listen and take things in. We’re like, well, let’s figure this out. Like, right now, like, I’m ready to go right. And they need to take time to think about things right. If you don’t understand that, you’re like, what’s wrong?

Jeremy Weisz 11:50

You could take offense to it.

Steve Whittington 11:51

Why can’t we make a decision? Why can’t we go right? And you’re like, are you indecisive? Like, you can — all these assumptions can pop up. So you really have to take that time and learn to understand each other how you work, and just the other side of it is unbelievable. We also used, and continue to use a company called Unstoppable Communications, and they teach us different types of communication techniques so we can call each other out on stuff like, for instance, somebody’s talking to me, and I’m interpreting it in a certain way, and I’m hearing something which isn’t what they’re saying. I’m just interpreting through my lens and hearing it. And now we have the tools that they could say, Steve, are you creating a story in your head?

What are you hearing when I’m saying this? And we can talk about this, well, what I’m hearing you say is this, and we won’t take offense to it. It’s like, we understand that I have a certain types of lens, and I see, hear it a certain way, and this person is trying to express this and so we can really be heard. And it’s so hard to put like, ROI, like, I’m a numbers guy, right? Like, so how do you put ROI in this kind of stuff, right? Well, I look at like, how fast can we work through issues? What kind of like distractions do we have from poor communication in the organization, how do people feel like that? They can be heard that stuff is so important and it’s hard to put ROI on it, but, I mean, every single team member has the comfort level to be able to call me out on my stories as the president, and they can just say, hey, can we have a conversation? Right? And all the partners are the same way.

And so I don’t know what the value of that is, but I know the working capacity of our organization is greatly increased because we have those communication tools and that emotional intelligence to be able to do that kind of stuff, and just gets rid of a bunch of other stuff that’s baggage, right?

Jeremy Weisz 13:50

It’s really interesting, because it’s like people are perceiving. Maybe they’re just sensing. They’re perceiving. Maybe you’re perceiving something, or someone else is perceiving, I mean, not the way they’re meaning for it to be perceived, and then they kind of, let’s have an open conversation about, I bet a lot of that helps people’s personal lives. They’re probably bringing the stuff that they’re learning from unstoppable back to personal life, right?

Steve Whittington 14:15

You have a new set of tools to communicate with your spouse, so for sure, and other important folks in your life.

Jeremy Weisz 14:23

You mentioned you’re very ROI-focused. How did Unstoppable Communications, using them, get brought to the table? Because I imagine someone who is more numbers-driven may push back against that decision initially.

Steve Whittington 14:40

Yeah, well, I was lucky in the fact that, as an executive, they were brought to the table without my support initially, and I was kind of on the fence about it, even though I had met them and was like looking at stuff, I knew we needed some coaches in another organization. So, they had a different way of showing up. And so I was intrigued and I knew we had different sort of challenges in the organization. We were in a family-run business with a lot of emotional attachments, and so they stopped all the stuff that was going on, all the stories and everything like that, and it really changed that culture there. So I had years of that with them, so I was the one that brought them to the agency, because I could see the impact right.

Jeremy Weisz 15:37

Love it. No thanks for sharing that I mentioned at the front of the interview about clients coming to you with certain struggles, and maybe what they think they struggle with and what maybe they actually struggle with. So can you talk about when clients show up for you and what are they saying they’re struggling with? And then you can walk through your process a little bit.

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