Episode 131: Time Blocking and Staying Motivated with ClozeLoop’s Haylee Taylor

Haylee Taylor is the top Account Executive at ClozeLoop, a revenue strategy firm that drives performance for Management, Sales, Customer Success, and Sales Enablement in the fastest-growing companies on the planet. In the less than one year she’s been with ClozeLoop, Haylee has watched over twenty sales teams have their best quarter in company history. The impact spans top of funnel pipeline generation to discovery and demo training, account management, management coaching, and all the way up to executives. She’s exactly where she wants to be after hitting 268% of her last software sales quota: training sales reps to crush bigger quotas and exceed their leadership’s wildest expectations.

In this episode, Haylee and Scott talk about Haylee’s sales origin story, from city planning to selling software and then selling services. Haylee reveals why she absolutely loves cold calling and how that led to one of her favorite sales stories of all time. Haylee also shares the three things she most attributes to her success. These include adaptability, her ability to be coached and her ability to be memorable both to her colleagues and to her customers. Haylee expounds on her role at ClozeLoop and speaks to her incredible sales results. Hitting and exceeding her number is one of the major things that helps keep Haylee motivated.

Haylee dives deep into the types of questions she likes to ask when prospecting clients. She shares the secret sauce of how she develops these lines of questions and provides some strategies and best tips for sales professionals looking to do the same. Haylee takes the audience through a typical day in the life, from her natural internal clock waking her up at 7am and her walks with her dog Goose to meditating and time blocking her calendar for cold calling and meetings. Haylee reserves the second half of her afternoons for podcasts, team meetings or training hours. Then she unwinds with dinner and a fun activity, like watercolor painting.

Finally, Haylee issues an actionable challenge to the audience. She urges them to time block their calendars and use the word ‘chunk’ when thinking about it. ‘Chunk’ those meetings together, find that extra hour or two to work out or do something that’s going to impact your workday.

What We Covered:

00:01 – Scott takes a moment to thank today’s sponsors RevenueGrid and QuotaPath
00:39 – Scott introduces today’s guest, Haylee Taylor
00:55 – The top three things Haylee attributes to her success
01:03 – Number One: Adaptability
01:49 – Number Two: He ability to be coached
02:26 – Number Three: Being memorable
02:53 – What being memorable looks like
03:28 – Scott takes a moment to thank one of today’s sponsors, RevenueGrid
03:54 – Haylee expounds on her role at ClozeLoop
05:02 – Haylee quantifies her sales results
06:33 – Scott thanks the final sponsor of today’s episode, QuotaPath
07:26 – The transition from software to services
09:10 – Haylee’s sales origin story
11:08 – What Haylee would do anything differently if given the chance
11:36 – Haylee’s favorite sales story
12:49 – Why Haylee loves cold calling and the strategy she employs
14:13 – Haylee’s proudest accomplishment
14:42 – Moving quickly, growing quickly
15:17 – The most challenging part of Haylee’s role
15:58 – How Haylee positions herself for success
19:38 – Haylee takes the audience through a typical day
21:25 – Haylee’s meditation practice
23:52 – Haylee’s tech stack
24:25 – The books, news, podcasts, and trade information that Haylee consumes
26:05 – Haylee’s sales philosophy and style
27:02 – Haylee’s favorite question to ask
28:07 – What motivates and drives Haylee
28:29 – Haylee’s family
28:59 – One of Haylee’s beliefs that the average sales professional would think is crazy
30:12 – What Haylee’s preparation looks like
31:28 – An average sales professional’s belief that Haylee thinks is crazy
31:49 – The most important lessons Haylee has learned throughout her career
32:51 – Advice Haylee would give to an upstart sales professional
33:36 – Advice Haylee would give to struggling sales professionals looking to reach that next level
35:20 – What Haylee wants to know about top sellers in other industries and tips for developing your own line of questions
36:18 – The importance of understanding your buyer personas
38:12 – Haylee’s process of getting referrals
40:08 – Haylee asks Scott about a typical day in his life
45:18 – Haylee issues an actionable challenge to the audience

Read the full transcript & show notes →

Tweetables:

“I think there’s something really special to be said about talking to someone who has no idea why you’re calling or what it is that you do but liked the way that you spoke or that you said something that resonated with them and that person has now been a customer for the last eight months.” (11:59)

“I would describe my style as invested in asking direct questions and getting truthful answers.” (26:29)

“I think the craziest thing I’ve heard is people not hitting quota for six months and being happy. I just can’t imagine being a salesperson and not being motivated by your number.” (31:37)

“Sadly, I think it’s a lot of times a habit that we’re built into to be thinking about talking about the product instead of talking about your buyer. How we build that into our model is talking about buyer personas daily.” (37:01)

Books Mentioned:

Triangle Selling

Sponsors Mentioned:

Quotapath
Revenuegrid