Sales Transformation

In this episode of the Sales Transformation episode, Collin talks to Kelsey Calabro, Customer Success Manager at Dooly, and the solopreneur behind heretic : the agency. Kelsey talks about her journey into the sales world, and what sort of hoops she had to go through in order to land the role that she genuinely wanted.

For Kelsey, it was a winding journey that allowed her to acquire a lot of skills that she otherwise wouldn’t have gained through a linear sales path. Kelsey found success as an SDR and an AE, but found that the role of the Customer Success Manager fit her the best.

Kelsey also talks about the challenges she faced with starting her own writing agency, and advises people to just get on with it: you don’t have to have everything figured out.

Show Notes

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HIGHLIGHTS

  • Entering sales via the support role 
  • Moving into a new state and acquiring a new SDR role
  • Job hunt tips: Build your own relationships with the company
  • Transition to CSM and enjoying the long game 
  • Try different paths in sales and see where you really fit 
  • Run into the water and figure it out
  • Starting a writing agency
  • You don't have to have everything figure out

QUOTES

Kelsey: "I wasn't the best cold caller. I'm not the best person that you meet on a call and 30 seconds I can pitch you and you see the value and you're like, yea, that was compelling enough. I had a lot of blind spots, a lot of weaknesses as an SDR. I'm definitely a better closer. And then for CS, that transition to Customer Success just really came down to, I like the adrenaline of sales, I'm just kind of tired of holding this heavy quota every month even though now I have churn and retention, and all these other things on my back, it's different."

Kelsey: "If you can, anywhere you're at, try to carve a path into different roles. AE if you're an SDR, don't be afraid to go backwards if you're an account executive and you want to try your hand in SDR work, that's great too."

Kelsey: "The vernacular of CS life is different. You have to learn a lot about advocacy and how you can champion and play into your customers. You're selling them constantly on the value, but you don't want to be a seller. So there's a fine line and a fine balance to walk there which was hard for me at first, as understanding the difference between demo and training and supporting and selling." 

Kelsey: "It is a role where you are given autonomy truthfully, and ownership. At the end of the day, if your accounts fail, it's the same as quota for sellers. Like if you don't hit quota, you got to look at your process. For CS it's the same thing. If your accounts aren't succeeding, you're gonna go back and keep tweaking your process and figure out how you can make it better."

Connect with Kelsey with the links below: 

Also, you can join our community by checking out @salescast.community. If you're a sales professional looking to take your career to greater heights, please visit us at https://salescast.co/ and set a call with Collin and Chris.

What is Sales Transformation?

Welcome to the Sales Transformation Podcast, the definitive stop for leaders driving change in the sales world. Hosted by Kevin Warner, we dive deep into the minds of Founders, CEOs, VPs of Sales, and Sales Development Leaders from trailblazing startups to industry-leading public companies.

Our mission is simple: to illuminate the path to extraordinary sales leadership. We explore a broad spectrum of sales territories, from the intricacies of Founder Led Sales and Outbound Sales to the transformative potential of Technology in Sales and Social Selling. Whether it's mastering your CRM, optimizing conversions, scaling sales teams, or engineering a complete Sales Transformation, our conversations are set to challenge the status quo and redefine sales success.

With a new content every day of the week, we bring you unfiltered interviews with the luminaries of sales, people who have not just succeeded but transformed the way we think about sales. Kevin Warner also shares sharp, tactical sales tips every week, packing decades of sales wisdom into bite-sized insights.

So, if you're ready to rewrite the sales rulebook and learn from the best in the business, the Sales Transformation Podcast is your ticket. Write us a review, share the show, and join us on this journey of sales evolution. Let's transform the way we sell, together!