PODCAST 168: How to Take Risks and Fail Fast with George Donovan


Humans have practiced the art of sales since ancient times. It is a profession that warmly embraces those willing to hustle. An eminently respectable way to provide for your family, and a safe road to financial security for an industrious worker.

The pandemic changed everything.

The sales industry could no longer rely on the traditions of in-person meetings. Companies scrambled to utilize new technologies to ramp up their virtual selling game.

In this episode of Sales Hacker, seasoned professional George Donovan, Chief Revenue Officer at Allego, offers up key insights distilled from his more than two decades of experience in sales, marketing, and operations.

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If you missed episode 167 check it out here: Announcing the Revenue Innovators Podcast

What You’ll Learn:

  • Find your confidence when you hit rock bottom.
  • Make mistakes, pay attention, play the long game.
  • Virtual sales are the new normal.
  • Leverage the latest in customer engagement technology and data to drive sales.

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Show Agenda and Timestamps

  1. Show Introduction [00:09]
  2. George’s Baseball Card [3:18]
  3. A Key Lesson [8:16]
  4. Making Mistakes & Coaching First-Time Managers [9:48]
  5. How Sales Has Changed [14:23]
  6. Adapting to the New Reality [18:59]
  7. George’s Biggest Influencers [25:06]
  8. Sam’s Corner [27:06]

Show Introduction [00:09]

Sam Jacobs: Hey everybody, it’s Sam Jacobs. Welcome to the Sales Hacker Podcast. Hey everybody, it’s Sam Jacobs. Welcome to the sales hacker podcast today on the show. We’re excited to bring you, George Donovan. George is the Chief Revenue Officer of Allego, a really cool company coming out of Massachusetts that’s building sales engagement technology and sales enablement and learning technology for salespeople. And George himself is a career salesperson. He started off selling fax machines on the streets of Boston and has since done a number of really interesting things.

Now, before we get into the conversation, we want to thank our sponsors. We’ve got three sponsors for the show today and this week. The first is Outreach. Outreach has been a longtime sponsor. In fact, they’ve always been a sponsor of this podcast, and they just launched a new way to learn. Outreach on Outreach is the place to learn how outreach does outreach. Learn how the team follows up with every lead in record time after virtual events and turns them into revenue. You can see how each one’s account base manages reps and so much more. Using their very own sales engagement platform, head on over to Outreach.io/OnOutreach to see what they’ve got going on.

This podcast is also sponsored by Pavilion. The community formerly known as Revenue Collective, Pavilion is the key to getting more out of your career. Our private membership connects you with a network of 1000s of like-minded peers and resources, where you can tap into leadership opportunities, training, mentorship, and other services made for high-growth leaders like you. With a Pavilion membership, you’ll build deep connections with peers to expand your expertise and unlock growth. Access a full suite of training and certification programs like frontline manager school, for sales, marketing, customer success, and unlock over 100 different job opportunities every week, shared between members in a trusted and private setting. Unlock your professional potential with a Pavilion membership now – join today at joinpavillion.com.

And finally, LinkedIn. Today’s virtual selling environment demands a new kind of approach, one that prioritizes the buyer above all else. As the world’s largest professional network with 722 million members, LinkedIn is the only place where buyers and sellers connect, share and drive success for each other every single day. Find new ways to connect with your buyers virtually with LinkedIn Sales Navigator – you can learn more or request a free demo at business.linkedin.com/sales-solutions.

Today on the show, we’re excited to have George Donovan. George is the chief revenue officer at Allego, responsible for achieving the company’s customer acquisition and sales goals. He’s a proven sales leader with over 20 years of sales, marketing, operations and management experience. George is a sales enablement enthusiast who loves tools and systems that empower people over the past decade. He’s worked with many of the world’s top brands to help them achieve their sales and profit goals.

Prior to Allego, George served as the Chief Sales Officer of Compete, the world’s leading expert in helping clients grow great brands in this role. George aided the exponential growth of the company from 30 million to 110 million. Previously, he was the principal owner of a Sandler Training franchise in Marlborough, MA for nine years. He holds a BA in psychology from St. Anselm’s College. He was also voted father of the year 20 times by his family in a contested election that many says was rigged with fraud. George, welcome to the show!

George’s Baseball Card [8:16]

Sam Jacobs: So, we start with your baseball card, which is really a way of giving you the opportunity to, in your words, tell us a little bit about what Allego does. I read a little bit about what they do – but in your words, what does Allego do, the company for which you’re CRO?

George Donovan: The formal definition? We’re a sales learning and enablement platform. We’re a software company. But to simplify and put in layman’s terms, what does that mean? We’re a platform for sales people to go to, to help them do their jobs. To gain knowledge, collaborate, seek coaching, anything that’s going to empower them to be more confident and more successful. That’s Allego. That’s the go-to place.

Sam Jacobs: How big is the company either from an employee perspective or a rough revenue range? Where are you on your journey?

George Donovan: We’re about eight years old, and we’re coming up on 200 employees. And as far as revenues, just sub 50.

From a young age, people always told me the same thing: you have the ability to get people to open up and talk and say things that they don’t necessarily say to other people. And I had so many people telling me that throughout my youth, that in my head, I thought I need to get into some sort of a career where I’m going to talk to people. It was either maybe a bartender or a psychologist, right? And so I went down the psychologist path.

I was an undergraduate in psychology, I was going to get my PhD in psychology. And at the last minute, I got cold feet, I didn’t want to keep going to school. I decided I’m going to go to work for a year, and then see if the psychology calling is still there. And I went into sales and on to finance.

To me, it was just like, what am I going to do for a year, I could get a sales job. So I was selling fax machines. This was the early days of fax machines in downtown Boston, knocking on doors, trying to convince people to buy this magic box that, by the way, was enormous back when fax machines first came out, and they were $2,000 apiece. And you put this magic piece of paper into one end into this machine in Boston and in New York, the paper would come out on the other end. So it was like some black magic to people. And it was tough. A lot of lessons were learned there in rejection and endurance, and just waking up in the morning with the right attitude.

A Key Lesson [6:51]

Sam Jacobs: What were the key lessons and principles that you taught yourself and told yourself in order to kind of move from a loss aversion/ negative mindset to a more gains-seeking growth mindset, where you’re looking forward to the day, because you mentioned that you loved it. What was it about sales that you love so much?

George Donovan: I was bottoming out fast. It was the first time I learned the lesson of fail fast. Today, that is one of our operating principles at Allego, that we teach every employee who joins the company to fail fast, make a lot of mistakes, and take risks. Because the sooner you do that, you gain more confidence. Because your bottom out, you’ve experienced so many things early, that then you feel like you can’t go any lower. It sounds funny, right?

But I remember the day vividly. I got hit over the head with a booklet in a law firm by an office manager who threw me, literally threw me out of the office, and hit me over the head with a stack of books. And I got on the subway home and started to cry. I had hit rock bottom in my sales career. I wasn’t doing well at the time, and now I’ve been assaulted. How could it get any worse? But that was the day I decided, okay, this is the bottom, I have nowhere to go but up. That empowered me and gave me some strange sense of confidence, which I think was the most valuable lesson I ever learned as a young seller.

Making Mistakes & Coaching First-Time Managers [9:48]

Sam Jacobs: Tell us about that journey, that sounds really interesting. What did you learn and what were some of the key mistakes that you made, that you’re teaching people not to make now that you’ve got some experience?

George Donovan: The first one was so obvious, but I had two goals. One was to make a number. The second goal was to build this team as fast as you can. Your audience is probably laughing because they’re competing goals. If you’re going to try to build a team too fast, you’re going to make mistakes, you’re going to hire the wrong people, you’re going to put the wrong people in the wrong roles. So I was actually paid to build the team quickly because we wanted to get a fast start, but that really incentivized me to make a whole lot of mistakes, which conflicted with the other goal of making a number. Looking back, that was a huge mistake from day one.

The other was just not really paying attention. We were selling in pods back then, putting three people in a unit in a sales pod, and not paying attention to people’s individual strengths and weaknesses and styles – trying to complement one another in these pods, instead of just haphazardly throwing three people into a group, which is not the right way to approach it. Right? You really need to have some consideration for the varying degrees and styles and personalities of the people in a workgroup. That was another mistake. And there were all sorts of mistakes around hiring the wrong people, bad incentive plans. In the beginning, you name it, I think I made it.

Sam Jacobs: What do you think the keys to great leadership and management are when you’re coaching first-time managers? What are you specifically focused on teaching them in order to enable their success?

George Donovan: The first thing you teach them is to be selfless. And that’s hard because a lot of first-time managers are coming from being an individual contributors. And as an individual contributor, it’s often about yourself and your goal. Of course, you care about your teammates. But now as you step into leadership, you are second, your team is first, your team takes priority, your needs go to the backseat. That’s a hard transition to make for a lot of people, to not put themselves first and to check their ego at the door.

The other is take off the superhero cape, you’ve probably heard this or seen this before. But you’ve got great sellers, who then become managers. And they continue to want to be great sellers, and they want to swoop in with their cape on and better their salespeople and sell for their salespeople. So they’re not teaching the salespeople and coaching the salespeople how to sell better, they’re actually doing it for them. Now, you have to do a little bit of that. But I see that as a huge mistake for first-time leaders and first-time managers – selling for people instead of empowering them to sell.

I think there are points in time where we all have to jump in and bail out a seller, as managers and as leaders, but it happens way too often. It all comes back to company culture, and the type of organization you want to run. And teaching people to play the long game. Not looking for that quick sugar high. Not thinking myopically about making each month’s number, but really building a team for the long run. Ingraining that into people from day one, so that they understand that it’s okay to fail. It’s okay to make mistakes, you’re playing the long game. If you miss a month, a quarter, or two, it’s okay, so long as we’re building for the long term. That’s a big part of our culture at Allego.

How Sales Has Changed [14:23]

Sam Jacobs: Do you think sales has changed since you started doing it? What’s your point of view? So much technology has entered the sales space, have the core elements of selling evolved or shifted, and if so, how? What have you seen change over the last, you know, 25-30 years?

George Donovan: The answer is yes. Especially in the last 24 months. I’ll give you some examples. I would say that the pace of change over the last 20 years was very slow-selling didn’t change dynamically. But the last 24 months have, you mentioned a whole bunch of great technologies, right? Allego, I believe, is one of them. We’re seeing this consolidation of technologies that empower salespeople around sales learning, sales enablement. There’s a lot of great technologies out there, and they are helping people.

What we’re really going to capitalize on now is virtual selling. The pandemic helped to magnify this, and the way that sales is changing. It’s prompted organizations to do studies around how do people want to buy now that virtual selling is more prominent? How effective are salespeople at selling in a virtual sales environment?

Is virtual selling here to stay? Or is it now just selling? Is that just the norm, in other words?

92 or 93% of buyers prefer virtual buying, rather than live interactions with salespeople. Right there, that tells you something. They have woken up and said, “okay, I like this, I like the new virtual aspects of buying.”

The other stat that’s interesting is that buyers are doing 60 to 70% of their research before they ever talk to a salesperson. I’m talking about b2b selling here. B2C is even worse, the numbers are even higher.

This is really magnifying the importance of having strong, capable salespeople. Because by the time you get face to face with a customer or prospect, it’s so limited now that you’ve got to capitalize on it, you have to add value, or else you’re done.

I could go on for a long time about virtual selling methodologies. We’re building something called digital sales rooms where buyers and sellers can engage and interact digitally. Really cool stuff on the horizon, and I think it will never go back, we’ll never go back to normal selling the way we did it.

Adapting to the New Reality [18:59]

George Donovan: The shift in skillset is I’m seeing that the people who are more organized, more analytical, are excelling in the virtual selling world.

We’re learning so much from analyzing call recordings and live game films where customers are talking to salespeople, and we’re learning so much about how they respond to each other, what words are resonating, what words aren’t resonating?

There’s so much to learn here. It’s incredible. The people who are really diving into it and learning these new statistics and capitalizing on them are the ones that are excelling.

We’ve got to learn these technologies, capitalize on these technologies, and we will. It’s going to happen, but it might force some people out of selling.

You’ve got to be super sharp, you’ve got to add value, you have to know your sh*t.

George’s Biggest Influencers [25:06]

Sam Jacobs: Who are the people that you think are inspirational, or that we should do a little bit of googling on or LinkedIn research on – people that have had a big impact on you, people that you think we should know about?

George Donovan: One is David Cancel. Dave is the founder and CEO of Drift, a company in Boston. He’s one of those rare visionaries, who also is one of the kindest people, and you’d love to have a beer with and just sit down and talk about life with.

And then my current CEO, Yuchun Lee, infamous for two things: super bright human being, he built Unica and took it public and sold it for half a billion. But prior to that, he was on the MIT card counting team for six years. Every weekend, he went to Vegas and made a lot of money doing that and learned a lot of life lessons. He’s a very unique and interesting person that people can learn from.

Sam’s Corner [27:06]

Hey, everybody, Sam Jacobs at Sam’s corner. Another really good conversation. We’ve only had great conversations here on the Sales Hacker podcast!

George is a career salesperson, and I just loved hearing about his journey, ditching his psychology degree back in the day and going door to door selling fax machines, and hearing how inside all great salespeople, all great leaders, is a sense of determination and commitment that just powers you through.

There are people that are just inevitably focused on the negative, focused on all of the bad things that have happened to them or could happen to them. And there are people that reframe the narrative in their minds towards a positive outcome. And to those people, sometimes rejection is only the fuel that lights their fire that pushes them to move forward.

We also talked a lot about the changes in selling and how digital tools and virtual selling is now just selling. In fact, he rattled off a really interesting statistic – 92% of buyers prefer virtual selling. It makes sense to a certain degree if you’re sitting in your living room or your home office. Do you want a stranger to come into your room or maybe into your work office? Some people really, really want to meet people in person, but many people don’t.

There’s a lot of introverts out there, people that want to mitigate and manage their interactions. One of the things that’s great about virtual selling is, inevitably, the meeting always ends on time, everybody’s got back-to-back meetings, and there’s no opportunity for dallying or lingering, and you can regiment your schedule in a much more disciplined way. And. frankly, build in time for yourself in an easier way than whenever when all of the selling was in person.

Are you working on the tools that are going to help you get better in this virtual selling environment? Using technology, being analytical, understanding data, all of that’s going to become even more important as tools like Outreach and Gong and others proliferate. It’s a really interesting point.

Before we go, we want to thank our sponsors. As you know, we’ve got three sponsors on the show. The first is Outreach, head on over to outreach.io/onoutreach to see how Outreach does outreach.

Our other sponsor is the company I work for. It’s a company called Pavilion. We used to be known as Revenue Collective – we just changed our name to accommodate the fact that we’re creating communities for all kinds of functional areas, not just revenue. If you want to learn more and unlock your professional potential and get that promotion, go over to joinpavillion.com and apply.

Finally, LinkedIn. Find new ways to connect with your buyers virtually, with LinkedIn Sales Navigator. Learn more or request a free demo at business.linkedin.com/sales-solutions.

If you’re not a part of the Sales Hacker community yet you’re missing out. Go over to saleshacker.com to sign up. If you’re listening right now and you like what you heard, hit that five-star review on your podcast listening platform of choice. It really helps us get this message out to more ears.

Want to get in touch with me? You can find me at linkedin.com/in/samfjacobs, or email me, Sam@joinpavillion.com. I’ll talk to you next time.

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