Blog

April 2, 2019

Career Path: Olivia Spector, Account Executive at Workable

What do the career path and day-in-the-life look like for an Account Executive at Workable?

We connected with Olivia Spector to find out!

Also, Workable is hiring! Click here for all of their job openings!


Where did you grow up?  What did your parents do for work?  

I grew up in Hopkinton, MA which is the start of the Boston Marathon. Both of my parents have had a few roles throughout my lifetime, and most recently they have gone into real estate together. My dad is also a commercial solar consultant. Before real estate, my mom was a pharmaceutical sales rep and stay at home mom while my brother and I grew up.

Where did you go to college?  What did you study and what were some of your initial jobs out of school?

I went to UMass Amherst and studied Marketing through the Isenberg School of Management. During my time as a student, I had many marketing internships across the real estate, hospitality, and market research spaces.

Right out of school I worked in Merchandising at TJX as an Allocation Analyst. It had been my dream to work there as my grandmother previously had as well. While I was there I loved working with product and strategic planning. Eventually, Rachel Bates (SVP of Sales and Marketing at Workable), recruited me over as an SDR at Workable. She had managed my internship program at Compete the summer going into my senior year of college. I’ve been at Workable ever since!

What has attributed to your success thus far and has helped propel you to the position you have now?

I am extremely motivated and competitive with myself. I think one of the keys to success in technology sales, is knowing what you are capable of and never settling for less. At Workable we focus on what is best for the customer and collaborating as a team, rather than competing with teammates.

Career development is my biggest motivation at Workable. I hate feeling stuck or unchallenged; personal growth and mastering new skills are crucial to keeping me motivated. As an SDR, I was constantly thinking about where I wanted to be next and I knew it was a springboard role here at Workable, with a lot of opportunities. Instead of focusing on the numbers I focused on building long-term meaningful relationships with customers.

What allowed me to progress upwards through four different roles at Workable in under two years is finding my voice. Communicating with leadership and establishing where I wanted to go, and aligning it with how I could add more value to the company while steadily increasing my responsibilities.

Can you share the high-level responsibilities of your current position as Account Executive at Workable?

At Workable, Account Executives get in touch with customers after the sales development team can qualify that the customer would be a good fit for the solution we provide. From there, Account Executives are responsible for demoing the platform, identifying a plan that works best for a customer, and supporting all customer needs throughout the software evaluation process. The team is responsible for conducting strategy calls with customers throughout the buying process to work through their team’s questions and build understanding and buy-in for the program internally.

Account Executives also work very closely with our Account Management team to ensure that the transition from purchase to implementation is as smooth as possible. There is a lot of collaboration with Support/DevOps teams to answer technical questions, as well.

Any tips for someone considering a career in Sales?

Plan on putting the customer first, and get to know them as a person the best you can. While it’s extra work, it builds a foundation of trust that helps you and the customer in the end. Technology sales is a very fast paced environment, so the most successful reps are the most organized. Finally, don’t force a fit with a customer; as much as it’s not fun to hear a “no”, there is a lot of value in providing a truthful and helpful sales experience!


Day in the Life


Coffee, tea, or nothing?

Nothing- although I desperately wish I liked coffee for an extra energy boost!

What time do you get into the office?

If I don’t have an early demo I like to be in around 8:30, and have a slower start to the morning.

What are three things that motivate you in your role?

Career development and new opportunities, contributing results to a team and learning new skills. I tend to get bored easily, so if I’m not challenged to learn something new or have a team goal to work towards I find it really tough to stay motivated. Thinking about where I want to be next is exciting and is why I always want to be learning new things.

Every day is different, but can you outline what a typical day looks like for you?

I get in and check salesforce to understand at a high level what I have going on for the day. From there, it’s prepping for demos, and strategy calls with clients. Of course with the nature of sales you can’t always pinpoint exactly what your day will look like as you’ll receive emails and calls you weren’t expecting. I also always block off a lunch break to recharge, which is strongly encouraged at Workable. We have an open space office where there’s lots of brainstorming and collaboration that happens impromptu throughout the day as well!

I always end the day looking at my calendar for the next day and doing any prep work I can before I head out so I don’t get stressed anticipating the next day.

What time do you head out of the office?

I tend to leave by 5:30 at the latest. Some days change a bit depending on when I have demos scheduled and the time of year but for the most part I can keep my true working hours from 9-5pm.

Do you log back in at night or do you shut it down completely?  

I don’t bring my laptop home. I’m the type of person where work and home don’t mix because I need to recharge. If I don’t set strict working hours for myself it’s a fast track for me to get burnt out (I had to learn this the hard way!).

Any productivity hacks?

Color coding my calendar is huge! I have different colors for client meetings, internal meetings and personal time to do tasks. Don’t be afraid to block off time that you need to recharge if it will actually make you more productive. Finally, find a system that works for you. For me, a to-do list is a must so I can visually see what I need to accomplish for the day.

What are the 3 apps that you can’t live without?

Instagram, Venmo and Down Dog. BTW Down Dog has awesome on demand yoga classes that are free!

What professional accomplishment are you proudest of?

I was the first person at Workable to ever be a Senior SDR and Junior Account Executive alongside a counterpart in our Greek office. The fact that the company trusted me to set the tone for two new roles is something I’m very thankful for.

Who do you admire or call upon for professional advice?

I’m lucky that both of my parents have been in the business world for years so I know I can always trust their input. One of my best friends from UMASS, Kali Hegarty, is another person who I always bounce ideas off of. She graduated one year ahead of me, so every time I need advice on something she’s tested the waters first. Finally, Braydon Gemmill-Beck and I have worked together at TJX, and have gone through the sales path together at Workable. There’s literally no one who understands where I’m at in my career better than he does!


Colin Barry is the Content Manager to VentureFizz. Follow him on Twitter @ColinKrash.

Images courtesy of Olivia Spector and Workable

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