Sales Leadership Advice: 17 tips from top sales leaders

The Dock Team
Published
June 25, 2024
Updated
June 28, 2024
TABLE OF CONTENTs
TABLE OF CONTENT

Ever wondered what it takes to become a truly great sales leader? The skills, mindset, hiring practices, and resources you need to become the very best at leading a sales team? 

Yeah, us too. So we sat down with 11 of the top sales leaders in the world and asked for their advice. 

They’ve led sales at companies like Facebook, Gong, Confluent, Loom, Intercom, and Mulesoft. And if there’s one common thread in their interviews, it’s this: 

What got you here won’t get you there. The skills of a great AE are not the same as those needed to be a great sales leader.  

So, what does it take to lead a sales team at a high-growth company in 2024? Here are the top tips from some of the best sales leaders. 

How to manage a sales team 

Stepping into the sales leadership role isn’t about being great at sales. It’s about making it easy for your team to be great at sales. To get there, our experts recommend that you: 

1. Be a player-coach

Tushar Makhija went from first GTM hire to VP not once but twice—first at Helpshift, then at Airbase. Today, he’s the CEO and founder of TeamOhana.  

His advice for effective sales management starts with gaining the trust of your sales team members: 

“To become a leader, first, you have to be accepted as a leader by the team. Then they let you become better at leadership.” 

And, to gain that trust, show them that you’re prepared to work alongside them on every task.

“I think my team quickly realized two things. I'm still in touch with many of them. They said, ‘You always led by saying, 'Let me do it first, and I'll show it to you,' rather than saying, 'Go and figure it out.'”

If there's a cold call, I'd make cold calls. I did cold email. I did all the demos. If I’m available, I'm on the demo with you. I think that was the trust. Then the leadership evolved from there.”  

2. Keep telling the story 

Tushar also reminds sales leaders that it’s your job to reinforce the company mission and vision with your team, especially in startups: 

“I think that, as a leader, you have to keep telling the story and not allow people to forget why we are here, how we all started, and how privileged and, I would say, lucky we are to be in this situation. 

Then use that as motivation to say, ‘Okay, what can we do to maximize the chances of success and try really hard to minimize chances of failure?’” 

3. Respect your team’s time

Jason Fishkind went from the first AE at Sprinklr to their Group Director of Sales, during which time the company grew from $5M to $500M ARR. When he moved to People.ai after Sprinklr’s IPO, Jason hired nine AEs in six months. 

He learned the hard way that you have to be mindful of your team’s free time: 

“One Sunday night, I sent an email at 9.50 pm Eastern. I walked back into the office on Monday, and my whole team is there for the Monday morning meeting. And one guy, he looks at me. He goes, “Jason, do you watch Game of Thrones?” I go, “No.” He goes, well, you sent an email in the last 10 minutes of the series finale of Game of Thrones. He's like, “This guy better have something important to say, or I'm going to kill him.” 

So you know what? I learned my lesson, and I definitely do not do that anymore. The send-it-later button or Slack later button is my best friend.” 

4. Let your direct reports learn through failure 

Loom’s first sales leader, Pete Prowitt, led sales from $1m to $7m ARR. Today, as the Head of Revenue at Stytch, the hardest thing for Pete to learn was “when to allow somebody to learn through failure.

One of my mentors told me early on, ‘When something is too big to let somebody fail, that's when you have to intervene. When you can actually let somebody learn through failure, it can be super, super powerful.’” 

5. Be consistent… 

As Gong's Head of Sales & Growth, Chris Orlob, helped grow Gong from $200k to $200M ARR before founding the sales learning platform pclub.io

He believes that “consistency is the key to running a sales organization. Because if you run a 50-person sales organization, you have to have everybody marching in the same direction, or else you just can't manage them.”  

Without a clear agreement on what you’re doing, deal stages, exit criteria, sales metrics, and so on, Chris says, “It's going to be Wild West very, very quickly. There will be no predictability in your revenue and your revenue motion.” 

6. …but stay flexible 

Jason agrees that there “needs to be some level of consistency. Just because there's not a time of the day to go be a full-fledged individual to everybody.” 

However, he also recommends being empathetic and adjusting your management style to each employee as much as possible. “For instance, this person, his or her strength is in how they communicate, but they struggle with deck building. Or, another person, they struggle to ask the tough question of a customer. Another one has something happening at home. In my day-to-day interactions, I really try to adjust accordingly.” 

7. Be a great listener 

Conor Dragomanovich says that high-performing AEs share at least one skill set with effective sales leaders: the power of listening well and asking the right questions. 

Conor rose from AE to VP of Sales at Productboard and led Sales at Vareto. These days, he’s on the go-to-market team of a little company you may have heard of — OpenAI.

“Much as with helping a customer solve problems, I felt like the value of a leader is the ability to really and truly listen with the right intentions and ask meaningful questions to help both the AE and then yourself uncover the productive learnings and carve the right path out.” 

As an AE, Conor spent serious time listening to Gong sessions, and he took the same approach when it came to managing his team, spending hours listening to recordings of his team’s calls and pulling snippets for later discussion and feedback. “It just amplifies the way you can work with an AE. You understand their approach. You're seeing it from the perspective of the customer.”  

8. Make mistakes—just don’t make them twice

Bryan Rutcofsky, former VP of Sales at Yext, grew the company's sales team to 140 members and about $100 million in revenue before leaving to co-found Marqii.

His top tip for sales leaders? 

“It's okay to f*** up. Just do it quickly, and don't make the same mistake twice.” 

Learn from mistakes, Bryan cautions, but “don't dwell on the mistake you made. There are too many people that will sit there and just wallow in the fact that they screwed up and can't move past it. Making a mistake is part of business. It's part of learning.” 

9. Find your “Why” 

As the former CRO at Lattice, Dini Mehta took the company from $3M to over $100M in ARR. Now Executive in Residence at Peak XV Partners, we asked Dini what motivated her to keep pushing herself. 

“I think having a strong ‘why’ really served me,” she told us.  

“When I was a rep, and I became successful, I was like, ‘I'm never doing any other job. This is amazing. I make a lot of money. I can get my job done in five hours a day. Why would I do anything else?’

Then, at some point, I was like, ‘I love coaching other people’. And so management became much more enticing to me. And so I did that. I was like, ‘This is awesome. I've got my team. I've got my culture. Why would I do anything else?’

Then, over time, I was like, ‘If I really want to change how sales orgs are built from the ground up, I've got to have a bigger seat at the table. I can be this manager and be happy in what I'm doing, but I really want to help change the game of how sales orgs are built. And so that became my why.” 

How to hire the right salespeople

Sales leaders need to have an instinct for finding top-performing AEs. Here are the top hiring tips from our panel of experts: 

10. Hire for curiosity and emotional intelligence

Jason Fishkind knows exactly what he looks for in new sales reps: 

“Curiosity goes a long, long way, and a mindset of wanting to learn. It can't be taught. You can teach experience. I can teach you sales process or what have you. But the other things are so critically important. Those are, to me, the two absolute requirements in folks that I hire.” 

11. Hire people who are better than you 

Marie Gassée spent two years as Confluent’s VP of Growth before heading up Go-to-market at Column. Her top tip for building a successful sales team is to “hire people that are better than you.

“The only way to scale is to hire folks who are smarter, more thoughtful, better than you, and who will remind you of it every day so that hopefully you can get a little bit better.” 

12. Hire slowly to protect your culture 

Even if you’re growing fast, Bryan Rutcofsky advocates hiring slowly.  

“In order to not upset the applecart, I can't bring in too many people whose voice will overpower the existing culture there today. 

“I try not to bring in more than 50% of a sales team at one given time. If I have ten sellers and I want to grow the team, I won't hire more than four or five in one fell swoop. Because I want the voice of ten to basically train and teach the voice of the five, not have another massive group coming in that can sway the culture and the attitude of the existing team.” 

How to get the support you need as a first-time leader

Top sales leaders don’t get there alone. Our experts agree you’ll need a solid support network to help you succeed. A few tips: 

13. Find a mentor

Before taking on his current role as CRO at Teleport, Hector Hernandez helped LaunchDarkly grow to over $60M in revenue and a $3B valuation. Three years later, he repeated his success with Traceable AI, helping them reach a $60M series B.

His advice for sales leaders is to find a mentor. 

“I always tell people that having a really strong mentor is worth its weight in gold. Having people that you can go to to help ask those silly questions. You're like, ‘Oh, man, I don't want to ask someone, but I don't know how I should structure a comp plan for an SDR. What should I do here?’

Having that community of people that can help walk you through stuff is amazing. That's definitely something that I think is needed.” 

14. Get an executive coach

Robby Allen, former Manager of Sales Development at Zenefits and now CRO at AgentSync, found executive coaching enormously helpful when he moved up into leadership. 

“It gave me this outlet to just be really vulnerable and really transparent about the problems I needed to solve[…] I think that the executive coach was a big unlock because he gave me this forum to name and define the things that needed to get done and then visualize a path to becoming that future.” 

How to level up your sales leadership skills

Wondering which areas you should focus on, when it comes to your own learning and development? Here’s what our sales leaders advise: 

15. Prioritize career moves that open up learning opportunities 

Rich Liu scaled sales at Facebook, Mulesoft, and Everlaw before becoming the CEO of Navan Travel. His career advice for sales professionals is to look for jobs that offer the greatest opportunity to learn. 

“I tend to think about careers as long things. As long as I'm still learning new things and reflecting and growing as a human and as a professional, by the end of it, hopefully, I'll be able to look back and say, ‘Hey, I grew. I had some impact. I created some memorable teams.’ That's really the goal.” 

16. Know your product  

Marie Gassée recommends that all sales leaders truly master their product knowledge. 

“When I joined Column in such a complex system, the financial system payments, I had a pretty tough come-to-Jesus moment: ‘Oh, I can't cheat here. I can't be cute and know just enough.’ 

“For the first time in my career, I had to go really deep into the product and really know and understand the market in a way that was, frankly, pretty humbling. My ability to be helpful as a sales leader or a go-to-market leader now is because I did the real work. And so I wish I internalized that earlier in my career.” 

17. Nail your sales pipeline reviews 

Conor Dragomanovich has some great tips for new sales leaders running their first reviews: 

“A good review should give the leader very clear visibility into the good, the bad, the ugly of their pipeline. It’s about answering the question, ‘Where are we exposed?’ That can mean different things. Where are we exposed in this specific deal? Where are we exposed in the context of our commit/most likely/best case, and so forth?”  

He recommends doing a pipeline check-in weekly, one-on-one, not as a team. That way, each AE can “look at their pipeline through your eyes and start to look for those exposure areas,” and you can help them work through any blockers.  

That way, when you get to a forecast call with the entire team, the process runs much more smoothly. 

Sales leadership training resources

Need even more resources? No problem.

In our 2024 B2B Sales Guide, we’ve built you a full list of over 100 vetted sources of sales wisdom to help get you started. Here’s a highlight reel for you: 

Sales reading list

A curated list of some of the best digital content about all things sales strategy, sales leadership, and sales process. 

Sales podcasts 

No time to read? No problem. Here are the podcasts every sales leader should be tuning into.

Want more sales podcasts? Check out our guide to the top 18 sales podcasts in 2024

Sales Communities

Want to actually talk to other sales leaders? Check out these top-tier digital communities. 

  • Pavilion - A (paid) private community focused on high-growth performers.  
  • Sales Hacker - The largest B2B sales community.  
  • RevGenius - Diverse and fast-growing community for revenue professionals. 
  • PreSales Collective - The largest global community for PreSales professionals and sales engineers.
  • Modern Sales Pros - Free community for revenue leaders in sales management, marketing management, and sales/RevOps. 

Or, you know, you could just go laugh at some sales memes. Sometimes memes help. 

Must have tools for sales leaders

Possibly, you just need the right tool stack to make your life easier. We’ve taken an in-depth look at the sales enablement tech landscape. Here are our top picks for sales leaders: 

CRM

The foundation for all the rest of it.

Sales training, learning management and content management 

Tools that help you share learning resources and sales collateral with your sales representatives and prospects.  

Conversation intelligence software

Automation tools that collect quantitative and qualitative data on sales calls, to help monitor sales performance, spot opportunities for sales coaching and refine product messaging.

Revenue intelligence software

Here are a few tools that help with forecasting and account health. 

Buyer enablement software 

Deal rooms (AKA digital sales rooms) let you set up a personalized buying experience for each customer. But they can also be a sales leader’s best friend. Dock’s modern take on deal rooms means that you can: 

Standardize your sales process and scale your expertise

Because Dock lets you create customizable, drag-and-drop templates of your customer-facing workspaces, it’s a great tool for onboarding new hires and bringing them up to speed quickly. 

Andrew Hollis, Director of Sales at Nectar, says that using Dock has helped his scaling team create a more consistent, elevated follow-up: 

“Part of scaling is that now we have this database of Dock templates—and ten reps creating them and innovating within Dock. Our reps can whip up these freaking awesome follow-ups in like three minutes. It's crazy. It saves them a lot of time. 

And so the first follow-up that a new rep gives is of the same tier as someone that's been here for two years using Dock every single day because they're copying that template.

I know exactly what they're saying and it's standardized. I don't have any doubts that they're giving the absolute best follow-up.”

Shorten the sales cycle and improve your close rate

Dock lets you follow up on your demos by sending prospects a workspace complete with demo videos, slides, testimonials, pricing information, proof of ROI, product screenshots, and other supporting sales collateral

This tool saves your prospects considerable time digging through their inbox, making the buying experience far more straightforward. In turn, this makes closing deals easier — Andrew’s team increased their win rate by 31% when they started using Dock.

Track buyer behavior and increase your forecasting accuracy 

Dock gives you real-time insights into your prospect’s interactions with your sales collateral—who is looking at what, and how often. Andrew says that Dock’s buyer engagement metrics help his team keep track of deal progress: 

“With Dock, we're finding who the high-quality accounts are. It's helping us decide who we target, and ultimately now I can pop in and actually see if the buyers are serious. 

If an AE thinks something's progressing, but the prospect isn’t really looking at the Dock—is it even possible?”

Read more about how Andrew and his team transformed their demo follow-up with Dock.

And, if you’re ready to level up as a sales leader in 2024, we’d love to hear from you. You can sign up for Dock for free, or get a personal walkthrough with one of our product experts.

The Dock Team