Kim Regan – Account Executive


Kim Regan recently became a National Account Executive at Achievers. She was interviewed as part of a 12 month Achievers Women’s Network (AWN) series. The series highlights women leaders at different stages of their career throughout the organization. Having worked with Kim for several years, I was excited to interview her and get to know her “behind-the-scenes”. Kim has a focused and determined energy that instantly draws people in. She’s a woman with a plan, has an idea about “who runs the world” and has great advice for women who shy away from Sales or other careers that “scare” them. But while she has strong convictions about women speaking up for themselves, supporting each others’ choices and doing sales “her way”, Kim has a unique ability to present sometimes harsh truths with subtly, empathy and humility.

Her Back Story

As we begin her story, I ask Kim why she seems nervous. She takes a breath before beginning, “My biggest hesitation coming into this is I don’t think I have an exciting story to tell and my initial reaction is why did AWN ask me? [Kim laughs as she slaps her own wrist, as if scolding herself] but then I asked myself “why am I thinking like that?” If AWN asked you there’s a reason! And if this is helpful or insightful in anyway to other women I’m happy to help.”

Kim sits up straight, across from me at a high-top table in her office, almost as if on a job interview. She straightens the sleeves on her white linen blouse and looks off into the distance before answering the first question. Talking about herself isn’t easy for Kim but within a few minutes she’s at ease and her charm, honesty and eloquence shines through in everything she says. It’s evident Kim speaks to prospects for hours each day – she thoughtfully chooses her words and paces her speech in a way that would captivate any audience…including me.

Tell me a bit about yourself and your journey so far.

I am professionally and personally very competitive. I’m driven by numbers, by metrics and by accomplishing my goals.

I grew up with two brothers, I was in the middle – a rose between two thorns [smiles coyly]. We were always playing sports, I competed in figure skating and gymnastics. I played varsity hockey, soccer, basketball and softball. I loved the competition of it, the camaraderie, the teamwork, pushing yourself, the fitness, the physical side of things. In sports, we were taught to set goals for ourselves, to have a plan to achieve those goals and to always have a next step in place.

I’m fortunate. My family is super tight and I get to see them every week. I always look to my parents for advice and guidance. I have so much respect for how hard they worked and the sacrifices they’ve made to gives us (kids) the upbringing we had.

Professionally, like a lot of people, my career is a winding road. After high school, I went to University of Guelph and completed a double major in Biology and Political Science. If you look at where I ended up today it doesn’t connect [laughs]. I liked the science side of things so I thought maybe one day I could be a doctor or physiotherapist and I’m not sure that I ever had a career path in mind for politics [laughs] but I didn’t want to pigeonhole my career when I was so young. And once I graduated I still wasn’t sure where I was headed so I took time to travel across Europe.

When I came back I got my first “real job” and it was my first taste in Sales.

Describe an experience that led you to where you are today.

Honestly, that first job in sales was a big one. It’s so different than what I do now but the core of it, is the same as my job today – working with people, building relationships and proving the value of what you’re trying to sell. That’s what I enjoyed about it then, so even though it takes on a different shape, having that first taste of sales, I thought I could turn this into a “career”.

I was working for a tour company in a downtown Toronto hotel. I’d give restaurant recommendations, provide directions and the other part of my job was selling tours. It was my first taste of commission and, hey, how much I got paid depended on how well I did and what I did [laughs] and that was appealing to me. When the company expanded to backpacking hostel sales I was tasked to knock on doors and cold call with no training whatsoever. My boss said “here’s a phone book, look up hostels and tell them why they should do business with us” and left me in a backroom to start calling.

I was scared as hell but you stumble through it. Oh I was awful!!! [laughs hard] People took pity on me they’d say “No. But you’re doing a great job.” I just butchered it at the beginning and that’s when I realized I’m much more confident speaking to someone in person [laughs and blushes]…I’m getting flashbacks!

What philosophy or piece of advice influences you?

I’m goal oriented. The biggest part of achieving a goal is having a plan. I will always have a plan in place. People make fun of my lists, I even have weekend to-do lists… “Fail to plan, plan to fail”. I believe having a strong plan is a crucial first step to get to where you want to be. Whether it’s a tiny project, a plan for the day or if you want to be a CEO of a company.

And something super simple that I catch myself thinking about all the time is what my mom always says…” treat people the way you want to be treated”. It’s so simple but people lose sight of that or get caught up in their everyday lives. Being kind, being grateful, expressing your gratitude and acknowledging people… it goes a really, really long way at work and personally. Keeping other people in mind is important.

What do you do to combat being your own worst critic?

I give myself a bit of a pep talk and as embarrassing as it is [starts laughing and leans in to confess]…..my girlfriends and I started this as a joke to get each other pumped up…but you know Beyonce’s song “Run the World”? Well, if I’m in the car waiting for a big meeting – I’ll think “who run the world?” Or I’ll text a friend to “send good vibes” and she’ll respond with “who run the world?!” It makes me laugh, it makes me relax and I’m like hell ya – I got this! [snaps fingers and chuckles].

I also “see” myself accomplishing my goals. When I used to play competitive sports, they taught us to visualize yourself skating a perfect program, standing on the podium or whatever your goal was. So now I’ll visualize myself crushing a presentation, having a great call or succeeding at a task that makes me nervous.

Kim Regan
“If you’re not doing something because you’re scared or it makes you uncomfortable that’s your number one indicator you should do exactly that thing. Put yourself out there, make yourself uncomfortable and learn to be okay with failure.”

Her Career Story

Tell me a about your current role as National Account Executive.

As an Account Executive, I work with prospective clients who are interested in Achievers’ product – mainly HR executives looking to implement a recognition and engagement solution. I spend a lot of time on discovery calls, doing demos of our platforms, presentations and pitches, proving our value. And working through contract negotiations to the point of signatures and implementation.

What the most challenging part of being in Sales?

There’s a lot of rejection in sales and I’ve learned to thicken my skin, to get tough and not take rejection personally. I put myself in situations where I’m uncomfortable or nervous on a daily basis – whether it’s calling a lead out-of-the-blue or public speaking. They definitely take me outside of my comfort zone.

I’m responsible for my pipeline and my results. It might take six months to a year to sell your first deal hopefully much less, but it can be challenging to keep on track and stay motivated when it’s so much work upfront for something that may or may not happen months from now.

What do you find most rewarding about your role?

[laughs and jokes] I know it’ll be rewarding when I sell that first deal. But seriously, because it’s such a long grind, you have to celebrate the little wins like booking a meeting or hearing back from someone you’ve been chasing for awhile. Those are the things that keep me going.

I genuinely believe in our product so it’s easy to talk about the impact we’ve had with existing customers in shaping their company’s culture, improving their engagement scores and their business metrics. To be able to truthfully tell those stories with conviction and passion while seeing everyone in the room nodding their heads is really rewarding because I know the product itself works.

Tell me about a risk you’ve taken in your career and the outcome.

I was hired at Achievers as a Customer Success Manager (CSM) 4 years ago. In that role, I worked with clients after they launched to grow their programs. I was successful in that role and was even the top performer on my team last year. I’m really proud of that accomplishment because it was so challenging. I had enterprise clients who were in rough situations when I took them over – I had to rally the troops internally and come up with plan to turn these accounts into success stories. And to see them become some of our most successful programs was rewarding.

Taking on this new Sales role has been my biggest risk especially when I had a role I was doing so well in and a team I loved but I felt I had progressed as much as I could as a CSM. I knew I was ready to make a move. There were two very different career paths I was exploring – I wanted to transition into a people leader role or take a big leap into my current role.

I struggled with the decision because being a people leader is a key part of my long-term goals but outside sales was something I wanted to get back into and what better place to do it than at a company you love and with a product you believe in. I wish I could say the transition was smooth or that it gets super easy after week one but everyday I learn something new and look forward to new challenges. And ask me again in a year if it was successful [laughs].

What advice do you have for women who want to pursue a career in Sales?

[without hesitation] Do it! I would highly recommend it! There aren’t enough women in sales! If you’re exploring it or want to get into it, talk to someone who’s in the role. Take a public speaking course, shadow a couple of deals, really learn about what’s involved. Sales is such a good role for women and it’s so often overlooked….[smiles and laughs] come on over to the dark side!  

You have to ask yourself and identify what’s holding you back. If you’re not doing something because you’re scared or it makes you uncomfortable that’s your number one indicator you should do exactly that thing. Put yourself out there, make yourself uncomfortable and learn to be okay with failure. I think it’s especially hard for women because as kids we’re taught there should be shame around failing and it’s frowned upon. We strive for perfection. We need to reposition failure because to fail is to learn something new. And if you’re looking to get into sales you have to be okay with stumbling, picking yourself up and learning from that experience.  

Identify where there’s an opportunity to improve – acknowledge it. Embrace it! Don’t be scared to say “this is something I can improve on and this is how I’m going to do it”. I think, as women, we try so hard to be perfect so externally we don’t want to admit our faults or our weaknesses so being able to accept them and then openly work on them is important. People can be scared to make a change, take a step back or sideways but if you want to be happy you have to do that sometimes. 

As a woman in Sales, have you ever felt required to behave or act in a specific way? 

Totally! A lot of the old-school training and traditional thought leadership in sales is around being this persona that’s competitive, aggressive and “pushy”. But being in sales is more than that, especially in the industry we’re in (HR). Our sales cycles can take over a year, we’re building a business case, proving our value to different stakeholders and establishing relationships with our prospects. There’s a lot of coaching involved. It’s such a long and complicated process, not a quick, hard sell. It’s big picture strategy discussions and it benefits you more to be personable or to be an advisor than it does to be a hustler or a traditional “sales shark”. I want to prove that women, or anyone for that matter, can have a wildly successful career in sales without taking on that stereotypical persona or those traditional sales’ traits.

When I told people I was switching to business development and into a full sales role, they were surprised and a little shocked. The response was “but you’re not salesy enough to do that job – you’re not aggressive enough.” At first I was a little ticked off but then I took it as a compliment. I thought good I don’t want to be this aggressive, macho salesperson. I don’t need to be that person to be successful! And then I thought “bring it on”, this is a challenge and if you don’t think I can do it then I’ll show you. It gave me the fuel I needed to embrace the challenge.

Kim Regan
“As women we are so hard on ourselves and we’ve taken this attitude of “you can do anything” to mean “you have to do everything! ”

Her Lived Experience

What does feminism mean to you? 

To me, feminism is a bit of a loaded word these days which bugs me, I feel like it’s such a label now. Of course, I’m a feminist! [Kim states this with indignation]. At it’s core, feminism by definition means equality…that’s what it comes down to. So feminism, to me, means believing in and striving for equality across genders. Everyone should be able to get behind that!

A lot of people are feminists without knowing they are and without labelling themselves. Does it mean that I think all genders are equal? Yes. Does it mean that I think all genders are exactly the same? No. To me, feminism is both men and women embracing our differences, celebrating our strengths and supporting each other without turning it into a loaded label.

What do you think the positive aspects are from having women in leadership roles?

Women that hold leadership positions or work in traditionally male dominated industries are paving the way and opening doors. Change is happening for women in my industry, it’s just happening slowly. I’m really lucky to be at Achievers. I was hired by, trained by and led by really powerful women who kicked ass and who became my mentors. I watched them move up in the company and be extremely successful. Also, because it normalizes women in all roles. That is not necessarily a trailblazer or pioneer – just someone doing what they feel passionate about and what they love to do.  And I look up to all these women.

Do you think are barriers are to a woman’s career advancement? 

Our generation has grown up being told you can do anything! Girl power! You have every opportunity available to you, you can do anything boys can do, and while I think that’s awesome…as women we are so hard on ourselves and we’ve taken this attitude of “you can do anything” to mean “you have to do everything!” You have to raise a perfect family, you have to children, you have to be a leader, you have to have a lot of money and be a great role model and make home-cooked organic meals, workout 8 days a week [speaking in a rapid and exhausted tone] and live this perfect life. And we’ve unfairly placed those expectations on ourselves and other women. There are a lot of challenges out there for women still but we’re often our own toughest critics.

What role do you think women play in our advancement?

Women have to empower each other. If someone chooses to stay home and raise their family we can’t judge or place expectations on them or if a woman chooses to work a 60 hour work week and tries to shatter the glass ceiling we can’t criticize or judge her for that either.

Women have to get better at speaking up, showing our value, proving our worth and asking for what we think we deserve. We have to learn to toot our own horns and be our biggest cheerleaders because we tend to be quiet, not share or ask for things. My group of girlfriends and I all chose very different career paths but our common thread is we all work very hard, we strongly believe in and keep each other accountable by encouraging each other to share our accomplishments and be proud of our work. No one is pushing us down but we have to get better at speaking up.

We also have to support each other. I love being a coach and mentor – taking new team members under my wing, spending time with them, providing advice and helping them learn from my experience and knowing that I served them in a coaching role is rewarding. I can’t stress enough, the value of having a mentor in or outside of your place of work. Having someone you look up to, you go to for advice and to learn from is huge!

Kim Regan
“No one is pushing us down but we have to get better at speaking up.”

One more thing… any recommendations to help inspire women in tech?

How I Built This: is a podcast I listen to that highlights a lot of women entrepreneurs and really gets you thinking because you learn from their ups and downs.

The Achievers Women’s Network would like to acknowledge & thank the “In Her Own Way” blog for inspiring the 12-month series.