Episode 111: Katie Jane Bailey is Living the Disco Lifestyle on a World Class Sales Team at Figma

Katie Jane Bailey is the top Senior Enterprise Account Executive at Figma out of San Francisco. Figma is the first professional-grade online tool created specifically for interface design. Born on the Web, Figma helps the entire product team create, test, and ship better designs, faster. Katie Jane is a naturally curious sales professional who came into the industry from a fairly unorthodox path. As a musical theater professional, Katie Jane was an accomplished singer, dancer and actor in productions ranging from Off-Broadway and national tours to extensive regional theater and concert work. But don’t tell Katie Jane that acting and sales have nothing to do with one another. Katie Jane has leveraged her performing skills to achieve a successful sales career.

In this episode, Katie Jane dissects her sales career from a multitude of angles, including the work she did on the largest deal in Figma’s history. Katie Jane identifies and analyzes three factors that she attributes to her success. These include her natural ability to perform, her curiosity and her innate ability to have difficult conversations and introduce friction into the client relationship. In Katie Jane’s mind, introducing friction and having those tough conversations is what enables the client-salesperson relationship to evolve and flourish. Scott and Katie Jane share their thoughts on value and expound on the concept of offering ‘no discounts.’ Katie Jane also provides her version of what a world-class sales team looks like and how she has worked diligently to cultivate one in her own organization.

Katie Jane believes that discovery is a lifestyle, not a stage. She’s a lifelong learner and that approach has paid dividends throughout her career. Katie Janes takes the audience through a typical day in the life, from her morning walk and Pilates session to her time blocking and an interesting email strategy. For Katie Jane, it’s all about capitalizing on those ‘golden hours’ where she can accomplish some customer-facing meetings and put in hours of prospecting. Finally, Katie Jane issues an actionable challenge to the audience in order to improve their results. She urges listeners to ask yourself how you can create a team culture within your team, who can you ask for feedback from and who can you provide feedback to in order to build a culture of a world-class sales team.

What We Covered:

00:01 – Scott thanks the sponsors of today’s episode, Proposify, Alyce and Vidyard
00:38 – Scott welcomes today’s guest, Katie Jane Bailey
01:17 – The top three attributes that Katie Jane attributes to her success
01:27 – Number 1: The ability to have difficult conversations and introduce friction into the client relationship
04:09 – Number 2: Katie Jane’s natural curiosity
06:54 – Number 3: Her natural ability to perform and host
07:52 – Katie Jane speaks to her non-traditional background in musical theatre and how she transitioned to technology sales
12:01 – Katie Jane talks about rejection in sales
13:04 – How Katie Jane leverages her acting skills while negotiating and selling
15:51 – How long before everything clicked for Katie Jane in her sales role
17:29 – Katie Jane explains her role at Figma
19:49 – Scott teases a project he and his team are working on and lets listeners know where to learn more
21:12 – Katie Jane quantifies her sales results
23:13 – Katie Jane recalls her favorite sales story, a major deal she landed for Figma
30:00 – Scott and Katie Jane share their thoughts on value and the concept of offering ‘no discounts’
33:54 – Scott takes a moment to thank one of today’s sponsors, Proposify
34:30 – Katie Jane continues her discussion on a major deal she closed
39:08 – How Katie Jane manages her time
42:19 – A valuable lesson Katie Jane has learned throughout her career
45:09 – Katie Jane finishes her story about the major deal she landed for Figma
55:50 – Learnings and insights Katie Jane gleaned from this sales success story
59:03 – Katie Jane takes the audience through a typical day in the life
1:01:29 – Katie Jane expounds on her practice of ignoring email for most of the day
1:05:52 – Other habits and routines that are critical to Katie Jane’s success
1:08:34 – How many of Katie Jane’s goals did she accomplish in 2020 and how often she reviews them
1:10:26 – Katie Jane describes her version of a world-class sales team
1:12:38 – Scott takes a moment to thank another sponsor of today’s episode, Terryberry
1:13:16 – Scott provides his definition of a world-class sales team
1:19:00 – The books, news, podcasts and trade information that Katie Jane consumes
1:20:55 – The most impactful books and podcasts Katie Jane consumed this past year
1:28:16 – Other tools and apps that are critical to Katie Jane’s success
1:29:31 – Scott and Katie Jane provide their overall thoughts on the double-edged sword of technology
1:34:51 – Katie Jane discusses why she does not subscribe to a particular sales philosophy
1:36:50 – Katie Jane describes her sales style
1:38:10 – Scott takes a moment to thank another sponsor of today’s episode, Alyce
1:38:56 – What motivates and drives Katie Jane
1:40:27 – What are Katie Jane’s goals as it relates to her sales career
1:42:43 – How Katie Jane manages her hyper-competitive nature
1:45:46 – One of Katie Jane’s beliefs that the average sales professional would think is crazy
1:47:34 – An average sales professional’s belief that Katie Jane thinks is crazy
1:53:01 – What Katie Jane would do differently if given the chance
1:56:59 – How Katie Jane helps others entering sales from non-traditional backgrounds
1:59:16 – Advice Katie Jane would give to struggling sales professionals
2:01:14 – Katie Jane shares her thoughts on what lies in store for her career
2:02:53 – What Katie Jane would want to know about top sellers in other organizations
2:07:30 – Katie Jane provides final words of wisdom to fellow sales professionals
2:08:39 – Scott and Katie Jane talk about the rapidly changing landscape of sales
2:12:05 – Katie Jane’s proudest accomplishment at Figma
2:14:06 – Katie Jane’s actionable challenge to the audience
2:15:37 – Scott encourages listeners to share this episode with your team

Tweetables:

“Having done this for a while, I think that friction actually creates intimacy with my customers, and I find that it can be a really good thing.” (02:31)

“One thing I had never done before this deal was sell internally to get buy-in on why we should work on this deal. And, this was a lesson in that, 101.” (38:09)

“I think that’s one thing that, as salespeople, we want to get the deal done at all costs. I think that sometimes the way I like to think about it is that we are the front line of protecting our company.” (49:42)

“As a rep, if you don’t have the courage to introduce that kind of friction, who knows how long that sales cycle would have gone on. Who knows how many more resources it would have taken from Figma to get that deal done?” (58:07)

“If we can be a world-class sales team, then we have to operate like a team. We have to celebrate each other’s wins, grieve each other’s losses, give peer feedback and see feedback as a strength.” (1:10:58)

“Have you ever been asked if you love winning or hate losing? Well, I would say that I hate losing.” (1:40:09)

“I’m not one hundred percent clear on where I want to go, but I know I want to be working with people.” (2:02:24)

What We Covered:

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