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Sales Leader Spotlight: Carrie Jeffrey’s Unconventional Journey To Sales Leadership

Meet Carrie Jeffrey, Account Development Manager at 360Insights. I had the honor of meeting Carrie last month at the Unleash conference in San Diego. She attended the #GirlsClub Women in Sales breakfast where I learned of her unconventional journey to sales leadership. I was inspired by her courage and confidence and excited when she agreed to share her story with our community. Enjoy!

As a young girl growing up in a very conservative religious culture in a remote town in Northern Ontario, my outlet into the “real world” was reading books. My admiration for stories about Nancy Drew and the Hardy Boys solving mysteries grew into a passion for the espionage thrillers of Robert Ludlum and Tom Clancy. My adolescent heart fell in love over and over again between the pages of romance novels, hidden between the mattress and box spring of my bed. From a young age, I yearned for something more: something thrilling and adventurous. Something beyond the constraints of my upbringing…I wanted to be more.

I yearned for something more: something thrilling and adventurous. Something beyond the constraints of my upbringing…I wanted to be more.

Changing high schools three times as my family relocated transformed that internal yearning into a longing for stability and security. My upbringing gave me strong messages about what success looked like as a woman: all the women I knew were married and had children. As the oldest of eight children, I had enough experience to set myself up for success! And so, 4 days before my 21st birthday, I got married and embarked on the road most traveled, the safest, most comfortable and easiest path I could take.

Suddenly, twenty years flashed past and I found myself approaching my fortieth birthday. It was a day of reckoning for me. I had fulfilled my expectations in life of marriage and motherhood, but questions assailed me. What had I accomplished with my life? Who was I? What would the next twenty years look like? When I voiced my questions to close friends, they reminded me that twenty years of marriage and raising four amazing sons was no small feat. Years of homeschooling (what was I thinking?), taking care of my mother-in-law, active service in our church, volunteering at my son’s schools, mentoring young men and women and running my own cake-making business definitely counted as worthwhile. But the fire that burned within me kept whispering “there’s so much more!”

A big career shift for my husband propelled me into chasing the “more”. Looking to start a corporate career in my 40’s was a little overwhelming at first…who could I convince to take a chance on me? What skills did I have to offer the corporate world? Would I be able to keep up with the demands of a full-time career? Did I have what it took to be successful? Where should I apply? What role was best suited to me? Ultimately all my questions drove me to take a step back and perform a self-audit on who I was and what fulfilled me as a person. After 6 weeks of soul searching, I came up with my mission statement: to live my best life and help others build better lives. I knew that any role I applied for would need to fit into this mission statement.

With this in mind, I applied to a local SaaS start-up for an entry level sales position. I had thoroughly researched this company and totally fallen in love with the idea of working for a company that had people at its core. Providing an unbelievable experience for its employees was one of 360insights’ founding pillars, and I was determined to join this unique company and find out what living my best life looked like. After 6 weeks of radio silence – no response to my barrage of follow-up emails, LinkedIn requests and phone calls, I tweeted a Starbucks coffee to the hiring manager aka a former Starbucks barista. My persistence and resourcefulness paid off with a job offer, launching my career in enterprise software sales.

My persistence and resourcefulness paid off with a job offer, launching my career in enterprise software sales.

Needless to say, there were some bumps and bruises along the way. Navigating the rough road of change was particularly challenging to my family as they adjusted to my new schedule, new friends and different priorities. After so many years of being the primary caregiver, chef, housekeeper, bill-payer, shopper, chauffeur, etc, it was tough on both my husband and the boys to assume some of my previous duties and share in the household chores. I was unprepared for that adjustment and initially attempted to do it all. I didn’t expect to feel the guilt and inadequacy when I realized I could not keep up. Due to changes in my workplace, I found myself serving in our customer success group. After a year in the role, I knew that my passion and strengths were in sales. Our CRO at the time spent my 5-minute interview pointing out how weak my CV was and how unsuited I was to work in enterprise sales. However, the saying “where there’s a will, there’s a way” held true for me, and I managed to convince my CEO to give me a chance to prove that I belonged on the sales team.

As I reflect on the past five years, I realize that the wisdom, strength, courage and plain old common sense learned through my life experience has sustained me through six role changes at 360insights as well as making the adjustments in my family and home life. All along, my story was being written with surprising plot twists and plenty of character development. I’ve learned to be grateful for all the experiences that have brought me to this point and not diminish them or count them as sub-worthy just because they don’t translate well on a resumé. It’s been surprising to discover that my story is worth sharing and may even help other women who find themselves writing new chapters in their lives. Today, I’m delighted to find myself coaching our Sales Development team here at 360insights. Taking on the challenge of people management has been incredibly rewarding and my team has enjoyed unprecedented success. I’m enjoying discovering the thrilling adventure of the “more” that’s out there and even more importantly, the “more” that I’m becoming.

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