Member Spotlight: Elizabeth Andrew DiGaetano

08/03/2016 8:24 AM | Anonymous


Name: Elizabeth Andrew DiGaetano
Job / Title: Senior Account Executive
Company: HelloSign
Industry: Technology, Enterprise Software, SaaS




What is the challenge that you are most proud of overcoming? Explain.

I’m not afraid of big challenges, yet reentering the workforce after 17 years of “opt out” is unquestionably the greatest hurdle I’ve overcome. Nothing prepared me for the uphill battle I would face to break back in. It took time and unwavering determination to change industries and get myself back into an exciting opportunity that is the right fit with my skill set.

It also happens to be one of the most rewarding things I’ve done in my lifetime.

How has your industry changed in the last 5 years, and what do you foresee as changes in the next 5 – 10 years?

When I came back into the workforce, I saw it as my opportunity to reinvent myself and decided to break into high tech. It took a few steps, but I’m now at HelloSign, a disruptive electronic signature company that makes it incredibly easy to sign documents electronically. I chose this role because it’s a great opportunity to return to a senior enterprise sales position and to utilize my experience to contribute to the growth of a company.

This industry has evolved a lot in the last 5 years – we are redefining the way businesses and individuals work by eliminating the hassle of having to print, scan, fax and/or snail mail important documents that require signatures. By making the signing process digital, we are helping people save time and money, and bringing companies into the future. I foresee this market only getting bigger in the next 5 – 10 years.

I’m in sales, and always have been, so from that perspective, a ton has changed over the years. No more rolodex, fewer face-to-face meetings, and huge technology advancements. At the heart of it, I think selling has changed mostly because buying has changed. With more information readily available online, consumers are better informed and prospects are much further along the buying cycle when entering the sales process. But, I embrace change. I’ve forged new territories, learned new markets, built teams from the ground up, raised assets. I strive to break new ground and make things grow – and to recreate myself. I foresee great changes ahead in technology and I’m super excited to be a part of it.

How have you grown your professional network? Explain.

I am a sales executive, so networking comes naturally to me. Not only was networking an incredibly effective way to exercise my sales skills, it was one of my most lucrative ways for finding work. I’d encourage anyone looking to expand their horizons, understand new technologies, or re-enter the field, to talk to people. Tell them you want to get back to work. Beef up your LinkedIn page and start connecting. Seek out networking events, and look for organizations to join. Read. Follow thought leaders and become a student of your profession. Know what events are going on in the marketplace.


When I made the decision to change industries from financial services to tech, I decided to attend a TechCrunch Meetup in the Presidio. I did not know a single person at the event, but I managed to meet two different CEOs standing in line for food trucks. Two years later, they are both still in my network and one of them is talking to me about integrating HelloSign’s eSignature API into his organization.

Be brave, as you have nothing to lose by connecting with people.

What tips do you have for other women just starting out in sales?

Sales is a digital game, with email campaigns, social media outreach, screen share demos, and such. It’s all about the sales stack, the technologies used during various stages of a sales pipeline to help accelerate sales productivity. We have an incredible amount of power at our fingertips to improve the sales process, and it’s a critical component for companies managing revenue goals.

But, it is easy to get lost in the tools. I work for a technology company and yet, to be successful in sales, you also need to be able to pick up the phone. Building a valuable distribution network with senior leaders takes more than making connections through social media. Control the sales process by connecting with people, providing solutions, and adding value. Know when to put the tools aside.

What role has mentorship played in your career?

I believe mentorship needs to be organic. It’s become a hot topic and a lot of people are seeking mentors but, in my opinion, the best way to find mentorship is through work projects. Mentorship, like any relationship, requires building trust. Working through challenges together lays a perfect foundation for this.

It’s true mentorship and executive sponsorship are needed to advance in leadership positions but, rather than ask “will you be my mentor,” try exposing yourself to new projects at work or through organizations where you can collaborate with others towards a common goal.

I had amazing mentors early on in my career. I am finding, once again, I have incredible mentors both on my team at HelloSign and through the CLUB Incubator program. I hope in some way to impart experience to my colleagues by mentoring as well.

What advice would you give to someone looking to grow in her career while making time for her family?

Family comes first, always. But you have to make sacrifices to grow your career. It’s a decision to make career a priority, and it means you can’t always be there for every event, every performance, and every game.Surprisingly, one of the best outcomes of returning to work has been the incredible impact it has had on my kids. It has made them better at taking responsibility for themselves, helping out at home, and contributing to the family. I was fortunate to stay home with my kids for many years but, by returning to work, it seems I’ve unintentionally become a role model for them and the ultimate career performance review was having my 17 year old son say, “Mom, I’m so proud of you”.

What do you like to do to unwind?

I love to spend time with my kids or hike with my dog. And, the beach is my ultimate happy place!

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