Welcome to Episode 42 of the Sales Influencer Series: the #1 podcast for modern B2B sales leaders. Enjoy the interview and take a look at our latest update to Ambition Coaching

For this interview, we welcome Ryan Taylor, the two-time Direct Sales Coach of the Year at Constant Contact

The topic of today's interview - the qualities of a great sales coach, and what it takes to build a scalable coaching process inside your B2B sales organization.  

Ep. 42: The Shortest Path to Success in B2B Sales

Interview Topics 

Ryan's Background. 0:00 - 7:09.

Less than 5 years into his career as a sales professional, Ryan has made 4 President's Clubs, earned two promotions, and served as a dedicated internal Sales Coach for Constant Contact's Colorado sales force.

As Sales Manager, Ryan oversees 8-10 direct reports and works in coordination with the company's Boston sales office to align processes and achieve revenue targets at the rep-level and team-level. 

Constant Contact was the very first company Ryan joined out of college. His first interview went so poorly, his manager told him he 'ate the pen.' He credits his success to one thing above all else - being the most coachable person in the room.  

Ryan also credits Constant Contact's onboarding and training program for salespeople. Ryan won a raffle ticket to attend a Broncos-Patriots game in his first few months with the company. That unlocked his competitive mentality. He also saw the excitement around President's Club. His manager told him what he needed to do on the phone to be successful. And Ryan ended up winning the March Madness sales competition. From then on, Ryan went to his manager and asked for feedback on how to get better and rise within the organization.

The Role of a Sales Coach at Constant Contact: 7:09 - 11:01. 

As a sales coach, Ryan would work with all the reps on the floor and do whatever it took to help them hit their goal and get better. Usually people would raise their hands or managers would ask to meet with reps to help make them better.

sales coaching apps

Pictured: Sales Coaching App Ryan Uses for 1:1's.

Ryan was surprised at the lack of repeatable processes among reps. He reached out to other sales coaches and managers and asked how they got reps to follow the process. He developed a philosophy called WIN Coaching.

WIN Coaching is an acronym. It standards for:

  • W: What happened?
  • I: Implications.
  • N: Next step.

Instead of force-feeding someone an answer, WIN helps people understand what's going on and come up with the idea for themselves as to how to be better - it's way more impactful. The goal is to help people have a 'click' moment, build a plan to fix it, then provide regular reminders and check-ins to help ensure the plan is being followed.

How Constant Contact Uses Tools for Coaching? 11:01 - 12:20.

Ryan uses Ambition and Salesforce to help give reps insight into their numbers - how they're doing, what their Activity and Objective scores are, and what they need to hit their goals.

salesforce sales coaching tools

Pictured: Ambition Visuals of Real-Time Salesforce Data

Salesforce reports also help Ryan and his peers drill more deeply into what reps are doing. 

Ryan's Philosophy on Sales Management: 12:20 - 19:06. 

Ryan has a great team he manages now. They are competitive and take ownership over their work. Ryan looks for people who are competitive, take ownership over their work, and are coachable.

Right away, Ryan puts new hires on a board against top reps. He switched to Sales Manager because some of the company's more senior managers - who had trained him - had moved on to new roles. Ryan found himself in a position to move onto being a manager and building his own team, so he could have total ownership over the development of reps and have the broadest impacts in his organization.

sales coaching dashboard

Pictured: 360° Coaching Schedule in Ambition

Ryan believes in hiring people who are hungry and coachable. Ryan's philosophy with training focuses on keeping it simple. Find the basics, drill them into new hires, and ensure reps can 1) close the bookends of the call; 2) ask the right questions to find the purpose of 'why reps want to use your product.'

The other philosophy Ryan has is feedback. He's looking for the right ways to give feedback - based on the feedback he gets from his reps - and models his feedback approach to meet them.

Lastly, to retain talent, Ryan believes that you have to value your reps. Show that you truly care about them. And they'll respond by crushing it for you, for the team, and for themselves.

How Constant Contact's Culture Creates Success. 19:06 - 21:33. 

Ryan credits Lauren Chacon and other sales leaders at Constant Contact (including his original manager, Mark Alig) for his ongoing growth and development as a leader. His colleagues in Constant Contact's sales leadership positions are great sources of influence and inspiration to Ryan.

Ryan also reaches out to senior reps on his team to get feedback on his own coaching. He gets phenomenal feedback from them and his sales coaches.

Top Challenges and Opportunities for Sales Leaders. 21:33 - 24:11.

There are reps who don't have confidence in themselves and their own process. Another challenge is finding new talent and keeping talent engaged. One of the other biggest challenges is that buyers aren't picking up the phone anymore. So that means Ryan and his reps have to adjust their processes appropriately.

Ryan sees big data as one of the best opportunities for modern sales leaders. Instead of throwing a dart at a board, you can now use buyer signals to reach out at the appropriate time.

Final Thoughts and Where to Contact Ryan. 24:11 - 25:32.

Ryan advises fellow B2B sales pros - be coachable. There are always people who can help you get better. The best ways to contact Ryan are via email at rtaylor@constantcontact.com or via phone at 970-203-7849.  

Huge thanks to Ryan for coming on the podcast. We are thrilled to have him and Constant Contact as clients here at Ambition - we hope you enjoyed this episode of the Sales Influencer Series.  

See 360° Salesforce KPIs in Real-Time with Ambition

Modern sales leaders use Ambition to enhance Salesforce KPI visibility and run supercharged sales reports, scorecards, contests, and TVs.

sales coaching app

Ambition has helped improve Salesforce KPI visibility for the likes of WayfairFiveStars, and Filemaker, and holds the distinction as the first sales management platform endorsed by Harvard Business Review,

Want bright lights on your Salesforce KPIs? Contact us.

The Sales Influencer Series Library

To check out further Sales Influencer Series podcast episodes, just click on the links below. 

Episode 1. John Barrows

Episode 2. Lori Richardson

Episode 3. Max Altschuler

Episode 4. Matt Heinz

Episode 5. Mark Leslie

Episode 6. Kyle Porter

Episode 7. Jon Bradford

Episode 8. Eks Anderson

Episode 9. Matt Hottle

Episode 10. Heather Morgan

Episode 11. Ilan Ferdman

Episode 12. Ryan Jenkins

Episode 13. Tamara Schenk

Episode 14. Mike Weinberg

Episode 15. Scott Britton

Episode 16. Mark Kosoglow

Episode 17. Dionne Mischler

Episode 18. Ken Barton

Episode 19. Kevin Karner

Episode 20. Jill Rowley

Episode 21. Brandon Redlinger

Episode 22. Will Wickey

Episode 23. Drew Woodcock

Episode 24. Dail Wilson

Episode 25. Nathan Sexton

Episode 26. Tucker Max

Episode 27. Bruce Tulgan

Episode 28. Dallas Hogensen

Episode 29. Morgan J. Ingram

Episode 30. J. Ryan Williams

Episode 31. Emily Mikailli

Episode 32. Lee Bartlett

Episode 33. Rex Biberston

Episode 34. Marcus Cauchi

Episode 35. Gary Vaynerchuk

Episode 36. Joe Gianni

Episode 37. Jason R. Jordan

Episode 38. Mike Kunkle

Episode 39. James Carbary

Episode 40. Skye PoVey

Episode 41. David Priemer

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