How to Inspire Salespeople with Ryan Precious

Helping sales professionals excel requires a unique and innovative approach. But what exactly does that entail? How can you attract top sales talent and elevate their performance? What strategies do the best sales leaders employ?

To explore these questions, Bart is joined by Ryan Precious, SVP of Worldwide Sales at ClickUp. Ryan shares his inspiring journey from BlackBerry to leading U.S. tech companies, detailing how his progressively executive roles shaped his approach to sales leadership. He emphasizes that exceptional sales leaders must excel in recruitment, lead by example, be data-driven and act as coaches who continually elevate their team's skills and performance.

Show Notes

0:24 Show intro
0:59 Welcoming Ryan
1:45 How they met each other
2:11 What's clickup
3:17 About Ryan's career dev
4:13 Starting with RIM
5:00 Started in sales and loved it
6:16 Going from RIM to Clickkup
7:22 App dynamics
8:57 Roxette
9:53 The 3 R's for sales leaders
10:11 (R)ecruit
10:29 (R)etaining
10:39 (R)evenue
11:23 How to recruit the best people
11:49 The rule of 3 in hiring
12:11 You always need to have a pipeline of candidates 
13:51 Selling before you buy
15:22 Four key areas to look for in an interview
17:22 What makes them special?
18:13 Understanding their "whys"
18:44 How to keep special people?
19:12 Get them off to a fast start
20:26 Look at the data and leading indicators
22:12 How to fend off poachers
22:56 Red flags 
23:28 Compensation and perks
25:10 Life enablement through sales leadership
25:59 Revenue
26:25 How can a sales leader drive performance?
27:02 Amp it Up -- book
27:10 Book: The Qualified Sales leader
27:51 Metrics are key
28:34 Economic buyer
32:14 Is Generational change affecting sales leadership?
32:49 More important than ever to have an IRL connection 
35:44 How to manage up in the sales hierarchy
37:12 Bart summarizes
38:11 Where can people find out more
39:48 Be a student of the game
40:00 Thank yous.
40:17 Outro

Audio Transcript

Ryan Precious: Yeah, I think the best way to, and this is how I try and lead as well, Bart, the best way to manage up is to manage down. If you're winning the hearts and minds of your people, you're involved in their difference, you understand their business, you're making a difference. Reporting up is easy at that point because you're driving the news, not just reporting it.

Bart Egnal: Welcome to The Inspire Podcast, where we examine what it takes to intentionally inspire. I'm your host, Bart Egnal, President and CEO of The Humphrey Group. If you've ever asked yourself how you can develop an authentic leadership presence or tell stories that have people hanging off every word, then this podcast is for you. And it's not just for executives; this is a podcast for anyone who wants to influence and inspire others in their work and life. My guest on today's episode of The Inspire Podcast is Ryan Precious, the Senior Vice President of Global Sales with ClickUp. Ryan not only manages a global sales team of 100, but he’s had a fascinating career path in tech, tech leadership, and building sales teams. Ryan, I'm really glad to have you on the pod to dive into that topic. Welcome to The Inspire Podcast.

Ryan Precious: Yeah, excited. Thanks, Bart. I appreciate the opportunity to share my story.

Bart Egnal: Yeah, and full disclosure here, we know each other through a long-time member of The Humphrey Group, your aunt, Cynthia Ward, my long-time mentor. So she's responsible for bringing us together, and I've got to give a shout-out to her. We're recording this on International Women's Day, and she's a pretty amazing woman.

Ryan Precious: She's the best. I've heard your name probably on and off for 20 years, so, likewise.

Bart Egnal: Likewise. It's kind of destiny that we had to do this.

Ryan Precious: Definitely.

Bart Egnal: Okay, so Ryan, give us the cliff notes. What's ClickUp? What are you doing? And then we'll step back and talk about sales leadership and what got you to this point.

Ryan Precious: ClickUp is a sales productivity platform. It helps internal teams communicate, work efficiently, save time, and really displace a number of tools that create a lot of internal noise. I joined ClickUp six months ago, helping to build and scale the sales team as we march towards an IPO in the next few years.

Bart Egnal: It sounds like building and scaling the sales team is a perfect fit with your skillset. Right now, sales is changing. How you motivate people is changing. What I really want to dive into today is your career story, but also how leaders who may lead sales teams, interact with salespeople, or have sales functions in organizations can lead and motivate salespeople. But before we get to that, take us through your career because, I mean, you're joining from Austin, but you grew up here in Ontario. So tell us how you got to where you are.

Ryan Precious: Yeah, I grew up in a small town in Ontario that most Canadians haven't even heard of. It's called Fonthill, in the Niagara region, between Niagara Falls and St. Catharines. I had a wonderful upbringing there with my parents and a younger sister. I went to university at Lakehead, took my undergrad in marketing and management, also studied my masters in business, and was a college athlete. I had a great collegiate experience.

Bart Egnal: What was your sport, Ryan?

Ryan Precious: Basketball.

Bart Egnal: Just like your sister, right? Because I know she was a star basketball player too.

Ryan Precious: That's right. Now, it's great to relive it with my oldest son as well. Wonderful experience there; wouldn’t trade it for anything. At that time, the largest Canadian tech company was Research in Motion, or RIM, as you probably recall. I'd love to say I had this burning desire for tech, even sales at that point, but RIM was just attractive for many different reasons—growth, it was a disruptive global technology.

Bart Egnal: Just to jump in for those who might not be familiar with the name RIM, you will undoubtedly remember BlackBerry. That was their device.

Ryan Precious: That's right. That's exactly it. No, good clarification. A lot of people, when they think of BlackBerry, they think of one of the original smartphones and understandably so. During my time there, I was always involved in enterprise software and services. I started off in sales and just loved it. From day one, the excitement, the competition, the hustle, sales being very quantifiable with always a scoreboard and leaderboard—it felt like a great fit. I had the opportunity early on to move into different leadership positions, which I was really grateful for because BlackBerry was going through incredible growth. During that journey at BlackBerry, I was asked by my VP at the time if I'd be interested in relocating to Dallas, Texas to help build the team from the ground up. That was my first experience leading teams and going to a new location with nothing but what I felt was a repeatable playbook and process. Recruit, hire, and develop a team, and that was a dozen years ago. I’ve been rinsing and repeating that model ever since.

Bart Egnal: How did you go from a brief foray into a two-year relocation to a twelve-year permanent move? You're married, you've got three kids. How did you go from sales leadership at RIM to ClickUp? I know you had some interesting experiences in sales and tech along the way.

Ryan Precious: Yeah, I'm a dual citizen now, and same with my wife who also joined the journey from Canada to the US. We have three American children, which is always fun to say. After RIM started going through some challenges, I had just received my green card, opening up external employment opportunities. From there, I joined App Dynamics in January 2015. It was my first experience with a Unicorn SaaS startup, a San Francisco-based company specializing in enterprise software for application monitoring. It was an incredible journey. I learned a ton. Up until that point, I was successful in sales leadership through natural abilities and hard work, but at App Dynamics, I learned from others about recruiting top talent, developing people, and inspiring them. The day before our IPO, the company was acquired by Cisco for almost $4 billion, a record multiple at the time. I stayed on for a couple of years during the integration but was eager for another startup challenge. The founder and CEO of App Dynamics founded another company called Harness, and I joined as a Series A company, employee 60. The company went through incredible growth, and in two and a half years, I built the sales team to 70 people. Then I moved to another startup, Rockset, experiencing similar ten-fold growth over two years. ClickUp was further along in their journey, and that was one of the reasons I joined them, in addition to their incredible product and strong executive leadership.

Bart Egnal: It's nice not to have to build from scratch and be able to take the next step.

Ryan Precious: That's right, a running start.

Bart Egnal: You've done the build from scratch, so really neat. All the different experiences of building sales teams and driving revenue. I know you mentioned the playbook. You talked about the system when we were prepping for this. You coined it the three R's. Tell us about the three R's in your system for sales leaders.

Ryan Precious: Yeah, I'll hit it at a high level, then we can go as deep as you want, Bart. It's about sales leadership and should be waking up, thinking, and breathing this every day. The first one is recruiting the best talent possible, typically the top talent at other companies. The second R is retaining that talent. Once you have A players, how do you keep them? The third R is revenue, around execution. If you get the first two right, the third becomes easier because you have the right people on board, developed, and retained, making revenue more manageable.

Bart Egnal: Let's dive into the first one. I think what's interesting is even though you're in sales leadership, the principles of recruiting talent, retaining talent, and driving performance apply to anyone building a successful team today. So let's start with recruiting. How do you go about finding and inspiring the best people, especially in this day and age with remote work, online applications, and AI?

Ryan Precious: Great question. Sales leaders spend a lot of their time on recruiting. It's their pipeline. Always having different candidates, whether you're a first-line leader, second-line leader, recruiting individual contributors or leaders, is crucial. There’s the rule of three with people at your company: someone might not make it, someone might surprise you, and someone could get promoted. So you always need a pipeline of right candidates. Recruiting the right talent is essentially a million-dollar deal. The impact of the right person is huge. So we obsess over big deals and need that same obsession over talent. Characteristics to look for include industry knowledge, tenure at companies, attainment to quota, and progression in roles. Using referrals and agencies can help. When speaking with candidates, it's about selling before you buy.

Bart Egnal: So tell me what that means. Let's imagine I'm a salesperson you've had your eye on. You’ve been LinkedIn-stalking me, know I’m a strong performer, but I’m comfortable and happy where I am. How do you sell me before you buy?

Ryan Precious: First, if you're comfortable, are you being challenged? Are you learning,growing? Just being comfortable in a role, in a job? We actually want people to get comfortable with being uncomfortable, being stretched, and learning. I’d typically start with a pitch, selling myself a bit, then selling the company and the opportunity. What does it mean to go through this type of hyper-growth? What does it mean professionally and financially to go through an IPO? I share stories of our top account executives having large six or seven-figure earnings years and the playbook we can teach them to be successful here. So, first, it’s getting them excited about the person they would work with, excited about the company, and then inspecting if they have the background and skills to be successful here.

Bart Egnal: And you mentioned there are four key areas you look for in an interview. What are those?

Ryan Precious: The first is intelligence, both IQ and EQ. We sell a technical product to a technical audience, so I expect them to pick up on the jargon and hold their own in a conversation. The second is overall drive. Top performers are typically the hardest working. The third is coachability. We want talent that’s been successful elsewhere but is also open to new ideas and learning a new playbook. The fourth is integrity. We need to trust they will do the right thing when no one is looking. Culturally, it’s crucial to get people who operate with trust.

Bart Egnal: What I love about your approach to recruiting is it starts with a vision. You have to inspire them because if they were ready to leave, they would have called you already. You need to lay out that vision for them, get them inspired, and then evaluate their capability in those areas. It really is about selling before you buy, right?

Ryan Precious: Exactly. We’re building a special company going through unique growth. We want special people. That’s somewhat subjective, but I have a soft spot for people with a sports background or who have achieved something special early in their career or outside of work. If they haven’t done anything special by 25, 30, or 40 years old, it’s unlikely they will at our company. It’s also about understanding their why—what drives them? Is it growth, earnings, promotion, development? Listen to the individual and understand their why.

Bart Egnal: Let's say you get someone in, and you get it right. Even with all that criteria, you don’t always get it right, or they leave. How do you go about retaining people? How do you inspire them to stay the course?

Ryan Precious: You go through all this effort to get someone in, and once they're in, you need to get them off to a fast start. Work with enablement or onboarding teams to prepare them from day zero. Give them competitive intelligence, product accounts, and start meeting with them. Pair them with a buddy system and connect them with peers to share best practices. Make them successful by giving them a warm book of business, leads, and reduce ramp time so they see immediate success. It’s about documented playbooks, data, and leading indicators in enterprise sales. Measure their activity, meetings, opportunities, and progression to coach them effectively.

Bart Egnal: I feel like you need an extra "R" between recruit and retain—"ramp."

Ryan Precious: That’s right. As they ramp up, measure their success through leading indicators and coach them based on data. After a year, when they are performing at a high level, they will get calls from competitors. Keep them close, understand their career aspirations, and celebrate their success. Incentives like President’s Club, compensation plans, innovative products, and internal promotions help retain them.

Bart Egnal: It’s about listening to what they need to reach their vision within the organization, whether it's products, compensation, or rewards. You almost become a life coach through sales leadership.

Ryan Precious: Exactly. It’s about deeply caring for your people, leading for them, and inspiring them to be the best versions of themselves. Great leaders can change people’s lives.

Bart Egnal: Let’s go to your last "R," revenue. Driving execution. How do you ensure your team delivers on performance?

Ryan Precious: Manage down and help get deals over the line. Selling is a team sport. Two books I recommend are "Amp It Up" by Frank Slootman and "The Qualified Sales Leader" by John McMahon. John’s acronym, MEDDIC, helps guide deals and mitigate risk. Metrics, Economic Buyer, Decision Process, Decision Criteria, Identify Pain, and Champion. Use these to guide account executives through deals, ensuring they cover all bases.

Bart Egnal: It’s about equipping your team to be effective, whether through frameworks, education, or modeling behavior.

Ryan Precious: That’s it. Explain the playbook, show how it’s been successful, and coach them through the process. Inspire them and lead them.

Bart Egnal: People have changed, leadership has changed. With remote work and AI, how have the needs of salespeople changed, and what do they need from their leaders now?

Ryan Precious: The basics still matter. Personal connection is crucial. Go see them in person, make an effort, and build personal relationships. True connection is more precious now. Whether recruiting or driving revenue, people still want to be inspired and led.

Bart Egnal: Last question. For those in the middle of the sales sandwich, how do they manage up and inspire their leaders effectively?

Ryan Precious: The best way to manage up is to manage down. Win the hearts and minds of your people, understand their business, and make a difference. Reporting up becomes easy because you’re driving the news. Be involved and lead from the ground up.

Bart Egnal: Great advice. Your points today are compelling for anyone building and leading teams. Understanding people’s "why," laying out a vision, working directly with them, and adapting what the company offers to help their vision come to life. Thanks for sharing your system, Ryan.

Ryan Precious: Appreciate it. I get excited every day. I’ve been fortunate to work with great people and have great mentors along the way.

Bart Egnal: For those wanting to become better sales leaders, what do you recommend they read or listen to?

Ryan Precious: "Amp It Up" and "The Qualified Sales Leader" are great. Also, the podcast "Grit." Be a student of the game, play the long game, work consistently, and give your best every day.

Bart Egnal: Great advice. Thanks for coming on the pod and sharing your story, Ryan.

Ryan Precious: Likewise. Thanks, Bart.

Bart Egnal: I hope you enjoyed that episode of The Inspire Podcast and the conversation with our guest. If you’re enjoying the pod, please rate and review it. Your comments and reviews help others discover the pod. Stay tuned for another inspiring conversation in two weeks. Thanks for listening. Go forth and inspire.