February 16, 2021

Balancing sales and wellness – Okta

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Alissa Masuda looks calm, cool and collected when we chat, taking her high-pressure sales job in her stride because she has a strong foundation of self-care and mindfulness. As co-founder of Greyback – a wellness and connection hub for women – she brings everything she learns there to her position leading Emerging Markets South West at Okta, selling cloud-based IT security software.

No more sales ‘bro culture’

When people think of tech and sales, they sometimes think of ‘bro culture’. Alissa is anything but that. With her open smile and a background in beauty before she moved into tech sales, she says there’s no bro culture at Okta.

“Okta is one of the first teams I’ve worked for that has a really professional sales team. From Sales Development Representatives all the way up, the level of professionalism is amazing.”


Alissa also brings her wellness focus to everything she does. She shapes her team culture, encouraging everyone to spend time on self-care, running a quarterly breathwork session, and being flexible with her team – which is fully supported by Okta’s company-wide approach to flexibility.

“Okta does have a great work-life balance. That’s a super buzzy phrase, and doesn’t mean anything if you don’t give people time off or give your team what they need to get mental headspace and clarity. We have unlimited vacation, parents can have specific hours or days they don’t have meetings and some teams have ‘no meeting’ days.”

Alissa says as a manager it’s important to stay connected with rituals that help you run a team without depleting your energy, and everyone (not just managers) need to ensure their own cup is filled. That allows people to bring their energy and their best selves to work.

Burnout to breakthrough

Alissa has worked in tech sales for nine years, joining Okta 18 months ago. Three years ago Alissa burned out at work. She was working long hours in high stress, got pneumonia and was very sick. That’s when she knew something had to change.

“I recognized that your body will turn off and physically stop you. That’s why Greyback is critical in my life.”

She co-founded Greyback, a self-care social club designed to empower women to feel more balanced and connected in their everyday life. Her meditation practice and everything she learns from their visiting experts helps Alissa stay grounded and have supported her career acceleration at Okta.


Okta is quite a technical product, so Alissa had to spend the first six months there really learning the product. She spent a lot of time travelling making corporate sales to big business, and was promoted to lead the Emerging Markets SouthWest team.

Alissa’s team is made up of 9 sellers, mostly new to sales, learning the role, learning Okta, and working out whether a job in sales is for them. Three of her team have been promoted under her mentorship, and she identified the skills that have helped people succeed:

  • Be curious. “They all ask a lot of questions and are very curious.”
  • Be independent. “The successful reps are autonomous in their work.”
  • Be an apprentice. “The people who do well listen to the best sales reps on as many calls as possible.”
  • Always work hard to be better than you were yesterday.

Learning from others is a key identified for success in sales – advice that applies across industries.

“You need to be thinking, who of the 100 people in the team can you look at and think you admire them, and ask what you can learn from what they do. You don’t have to be techy to succeed. You have to appreciate what Okta does. We’re the best in the business, we have an amazing team. You have to believe in what you’re selling or you won’t be successful, whatever it is.”

Now with COVID the sales roles at Okta have shifted everything online. It’s presented some challenges, but Alissa is confident in her team’s ability to perform.

“You can do almost everything remotely with Okta. Sales is all about human connection, so we use Zoom and turn on our cameras.”

When prospecting with clients Okta still send lunches, and do virtual campaigns – such as a virtual whiskey tasting – to secure meetings.

How boundaries give you freedom

We were amazed by everything Alissa fits into her days, and asked her how she manages to do everything. She admits it can be hard to switch off in sales, because your work is directly linked to compensation.


“You’re in charge of your own destiny. But I also set boundaries. Between 12 and 1pm I block myself out and my team tries not to book me, so I can get up and get food. I have a hard boundary at the end of the day, and after that is when I can do Greyback work. Sometimes there is so much going on that I take an hour after work to clear my head and really prep myself [for moving onto Greyback work].”

We asked her tips for setting and maintaining boundaries – because we often start out with the best of intentions, but they can be hard to maintain – and she shared:

  • Get comfortable being uncomfortable. “Some people are people pleasers and say yes even when their internal dialogue is saying no, I can’t take on any more work. You need to not take on so much and get comfortable saying no.”
  • Start with yourself. “The way to start is setting boundaries with yourself. Then you can set them with others. For example, if your calendar says you will eat lunch at 12pm, then you get up and you do it.”
  • Be gentle with yourself. “Make sure that if you don’t complete that activity you’re not beating yourself up about it. Seek compassion and grace for yourself.”

The advantages to having boundaries with your work and personal life is increased autonomy, better health and avoiding burnout – all lessons Alissa learned in previous companies where work took over her life and she burned out.

“For me wellness is whatever makes me feel balanced and at peace. That changes every day, especially with COVID, 2020 in general, and the election. Self-care is fluid depending on what you want in your life, it can change from meditation one day, to yoga, to saying no and setting boundaries. It’s prioritizing you every day. It’s not a selfish act, it’s a necessary act to take the best care of everyone around you, including you.”


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About the Author
Samantha Sutherland is the Chief Storyteller at WORK180. She is a Diversity and Inclusion specialist with an analytical background, making her work evidence-based and data driven. Host of WORK180’s Equality Talks podcast and her own Women at Work, Samantha divides her time between interviewing amazing women for WORK180, mentoring and coaching women in, or aspiring to, leadership roles, and providing high-level advice on diversity practices to Australian corporations. You can learn more about the Samantha Sutherland consultancy at samanthasutherland.com.au.

Looking for a new opportunity?

Our transparent job board only has vacancies from employers we endorse and lets you see what benefits, policies and perks come with the job.