Jenna Phillips was the top Account Executive at Jobvite and has recently joined Authenticx as one of their first Enterprise Account Executives. Authenticx was founded to analyze and activate customer interaction data at scale in order to reveal transformational opportunities in healthcare. Jenna is a relentlessly hard worker and is super competitive. Those traits, coupled with her personality and willingness to be a team player, have helped transform her into an ultra-successful salesperson. She’s smart, driven, accountable, and a natural leader. Jenna truly cares about her clients and goes above and beyond to exceed her clients’ expectations.
In this episode, Scott and Jenna talk about her sales origin story and discuss Jenna’s favorite sales story. Jenna speaks to some of her sales beliefs and philosophies that have shaped who she is today. Jenna shares her outlook on the relationship between Account Executives and their SDRs and why she believes that investing in SDRs is as valuable, if not more so, as investing in prospecting. Jenna talks about the leap she made from Jobvite to Authenticx and teases the fifteen questions she asks start-ups when she goes for an interview. She also shares the three things she attributes to her success which include being scrappy and quick on her feet, having a ‘Quarterback Mentality,’ and building quick trust with prospects.
Finally, Jenna issues two actionable challenges to the audience. She urges them to think about the question behind the question. If you’re going to ask a question that you would typically ask in any sales process, what three other questions should you ask to follow up on that question. As you’re prepping for a conversation, think about these questions in order to go deeper. Next, she challenges them to look with a very critical eye at what you want your legacy as a sales professional to be at the end of your sales career. Reflect on what levels you want to reach, what gaps you need to overcome to get there, and what resources do you need to lean on in order to achieve that.
What We Covered:
00:01 – Scott takes a moment to thank today’s sponsors Outreach, Proposify, and Terryberry
00:37 – Scott introduces today’s guest, Jenna Phillips
01:00 – The top three things Jenna attributes to her success
01:09 – Number One: Being scrappy and quick on her feet
01:55 – Number Two: Having a ‘Quarterback Mentality’
03:19 – Number Three: Building quick trust with prospects
03:55 – How to build trust
05:27 – Scott takes a moment to thank one of today’s sponsors, Vidyard
05:53 – Jenna expounds on her journey from Account Executive at Jobvite to her current role at Authenticx and quantifies her sales results
07:32 – Jenna’s sales origin story
11:26 – The journey from Jobvite to Authenticx
15:05 – Scott takes a moment to thank another sponsor, RevenueGrid
15:32 – Jenna’s favorite sales story
21:22 – Jenna’s proudest accomplishment
24:01 – Jenna’s Fifteen Interview Questions for Start-Ups
28:09 – The most challenging part of Jenna’s role
31:04 – Jenna takes the audience through a typical day in the life
35:32 – Tasks vs. Goals
40:25 – How Jenna approaches her relationships with her SDRs
42:43 – How much time Jenna spends prospecting each week
43:47 – How Jenna structures her work week
47:33 – Scott takes a moment to thank another sponsor, Gong
47:43 – Jenna’s tech stack
49:06 – The books, news, podcasts, and trade information that Jenna consumes
53:26 – Jenna’s sales style and philosophy
1:05:29 – What motivates and drives Jenna
1:07:52 – One of Jenna’s beliefs that the average sales professional would think is crazy
1:10:30 – An average sales professional’s belief that Jenna thinks is crazy
1:15:02 – Advice Jenna would give to an upstart sales professional
1:19:12 – Scott talks about one of his very first Daily Sales Tips and teases this year’s Sales Success Summit coming October 2022
1:21:02 – Advice Jenna would give to a struggling middle-of-the-pack sales professional
1:26:13 – What Jenna would want to know about top sellers in other industries
1:28:03 – Jenna issues two actionable challenges to the audience
“I feel like in my career I always envision myself on a treadmill. And, if the incline on the treadmill doesn’t feel like it’s high enough – meaning it’s not hard enough, it’s not challenging me and stretching me and making me better tomorrow – then I get itchy. I need to be where there’s a lot more challenges around me.” (13:39)
“I don’t believe luck exists. I think it’s where preparedness meets opportunity.” (22:49)
“I’m always looking at my number that I’m expected to close for the year as a task item. I don’t view it as a goal. I view it as a task. That is in my job description to do and that is what I committed to the company to do.” (35:48)
“I think that an hour spent developing your SDR is a bigger investment into your week than an hour spent prospecting. And I think if we invest in the relationship with our SDRs, it benefits us tenfold.” (41:23)
“Trying to fit into somebody else’s mold is gonna exhaust you. You have to figure out what gives you energy and can keep you moving in your process.” (1:04:31)
2022 Sales Success Summit
ALL Enterprise Sales Episodes
ALL SDR Episodes
Jenna Phillips on LinkedIn
Jenna’s Peloton Username: JPhillzzz
Scott’s Peloton Username: SalesTechScott
Jenna’s Fifteen Questions she asks when interviewing a start-up she’s considering joining:
Funding and Financial Health:
- What is your monthly burn?
- What is your current ARR?
- How many shares do you have outstanding?
- How many rounds of funding have you done (if any) and how much do you plan on raising in your next round?
- What is your runway?
Product (if a software company):
- Do you own your own IP?
- Do you have a recorded demo or can someone give me a live demo of the product?
- Who built the product and how was it built?
- What other similar companies (if any) are out there and what makes them different? Why have they found success or not?
- How many years of experience does the collective leadership team have?
- Have they founded other start-ups before? What were the outcomes of those start-ups?
- Why did they decide to start this company?
- Are there any previous sales hires? If so, why are they no longer at the company?
Sandler Sales Method
Miller Heiman Sales Process
Jim Brown on LinkedIn
Brian Kavicky on LinkedIn
Ian Koniak on LinkedIn
Jamal Reimer’s Book
The Question Behind the Question
The Challenger Sale