If you're looking to break into tech sales, you might be wondering where to start and how to succeed in this competitive industry. Our latest podcast guest Kaitlen Kelly, an experienced sales leader, offers an inside look at what it takes to transition into tech sales and thrive.
Kaitlen shares her personal journey, moving from a non-sales background in fashion to a high-performing Sales Development Representative (SDR) role. Today, she leads sales teams and is about to embark on her next adventure at the EdTech company Multiverse. Her story is full of valuable advice for anyone looking to break into tech sales ****and carve out a successful career in this field.
From Fashion to Tech Sales: A Bold Career Move
Kaitlen’s career didn’t start in sales. She spent seven years in the fashion industry, working her way up the corporate ladder, but soon realised that her path wasn’t aligned with her long-term goals.
"I was working as an analyst in the fashion world, but I wasn’t excited about the future. I had friends who made the switch to sales, but I was terrified of cold calling," Kaitlen recalled.
It wasn’t an easy decision, but after careful reflection, she decided to bet on herself and break into tech sales at 27, starting in an entry-level SDR position. This pivotal decision set her on the path to becoming a successful sales leader.
What is an SDR?
For those unfamiliar with the sales landscape, an SDR (Sales Development Representative) is often the entry point for people who want to break into tech sales. This role focuses on generating new business leads, usually through cold calling or emailing, and is critical for building top-of-the-funnel sales pipeline.
Kaitlen describes the SDR role as the "foundation" of a sales career. "It’s where you learn the basics of business acumen, prospecting, and resilience—all key skills for anyone serious about breaking into tech sales."
Building Resilience: The Key to Success
Sales is often described as a "roller coaster" because of its highs and lows. Resilience is a must for anyone wanting to break into tech sales. Kaitlen stressed that success in sales doesn’t come from a perfect playbook but from persistence and adaptability.
"No one hands you the perfect guide on how to succeed in sales. You have to figure it out as you go, and you’ll face rejection. But that’s part of the journey," she said. "It’s important to learn how to show up as your authentic self and not be afraid of failure."
For Kaitlen, getting comfortable with being uncomfortable was key to her growth. "I used to have severe anxiety about public speaking and taking risks, but I forced myself to face those fears. The more you do that, the more you realise that you can handle anything sales throws at you."
The Unexpected Perks of Tech Sales
While sales is often associated with hitting targets and making money, Kaitlen highlights other rewards of the profession—rewards that make it an attractive career for anyone looking to break into tech sales.
"Sales has given me access to so many different types of people and industries. You learn every day, whether it’s from customers or colleagues. It’s helped me become more confident and exposed me to experiences I wouldn’t have had in my previous career," she explained.
Kaitlen also emphasised the variety in a sales career: "No two days are the same. One day, you’re talking to a startup founder. The next, you’re learning about a new industry. It keeps things exciting."
Advice for Those Looking to Break into Tech Sales
Kaitlen offered three crucial pieces of advice for those considering a career change into tech sales:
1. Write Down the Risks of Not Taking Action
Kaitlen's first tip for anyone wanting to break into tech sales is to assess the risks of not making the move. “What will you lose by staying where you are? Often, the risk of not taking action is greater than taking the leap.” Reflect on the potential opportunities sales can offer, from financial freedom to career growth.
2. Speak to People Already in Tech Sales
Want to know what life is really like in tech sales? Kaitlen advises reaching out to current SDRs or sales professionals. “Talking to people who have already made the jump is key,” she says. This helps you understand the day-to-day tasks, challenges, and rewards of those who have successfully broken into tech sales.
3. Bet on Yourself
Kaitlen’s final piece of advice is to believe in your own potential. “You are in charge of your career path. If you want to break into tech sales, you have to trust that you’ll figure it out along the way,” she explains. Sales is about resilience, learning, and adaptability, and betting on yourself is the first step.
Kaitlen's Mantra: Her Favourite Quote
Every week on our podcast, we ask guests to share their favourite quote. For Kaitlen Kelly, a seasoned sales leader, her go-to mantra is from the movie Talladega Nights: The Ballad of Ricky Bobby
“If you’re not first, you’re last.”
This quote perfectly captures Kaitlen’s competitive spirit and relentless drive for success. It’s a simple yet powerful reminder that in sales, staying ahead and pushing yourself is key. Kaitlen’s journey, from cold-calling at age 15 to leading high-performing sales teams at top tech companies, shows just how true this mindset is.
In her words, this quote keeps her striving to improve and achieve her best in every situation. For those looking to break into tech sales, Kaitlen’s philosophy is a great example of how determination and confidence can lead to incredible results.
Tech Sales: A Career with No Limits
Kaitlen’s story is a perfect example of how taking risks and betting on yourself can lead to extraordinary success. For anyone looking to break into tech sales, her journey shows that it’s not about having the perfect background—it’s about determination, adaptability, and resilience.
"Sales has changed my life in so many ways. It’s a career where the sky’s the limit, and the rewards are worth the challenges," Kaitlen said.
If you’re thinking about breaking into tech sales, this podcast episode is a must-listen. Kaitlen’s experiences and advice will give you the confidence and insight you need to make your own leap into the exciting world of tech sales.
Listen to the full podcast episode here and start your journey into tech sales today!