“Encourage A Round-The-Clock “Pay It Forward” Mindset” With Helpshift CEO, Linda Crawford

“Encourage a round-the-clock “pay it forward” mindset. Dedicating work hours towards employee volunteering is great, but paying it forward…

“Encourage a round-the-clock “pay it forward” mindset. Dedicating work hours towards employee volunteering is great, but paying it forward should be an everyday occurrence. That includes being appreciative and regularly showing gratitude towards peers and supporting staff who allow everyone to succeed both personally and as a team.”

Recently I had the opportunity to interview Helpshift CEO Linda Crawford for the ongoing series: CEOs Share 5 Ways to Improve Your Company’s Culture! Linda Crawford came out of retirement to join Helpshift as CEO in September 2017, and her decision was largely motivated by the opportunity to empower female leaders and help shape the future of women in tech. Her previous roles include Chief Customer Officer at Optimizely and Executive Vice President of Sales Cloud at Salesforce.

What are the 3 most important values that your company’s culture is based on?

  • Trust: This is the key ingredient to ensure accountability, respect, and an overall healthy culture.
  • Customer Success: We equip our customers with the tools they need to serve their customers, so ensuring their success is an integral value for us.
  • Bold: We have amazing people and product, and we’re in a great position challenge the status quo — so that’s exactly what we are doing.

Managing millennials can often be a polarizing topic. Can you elaborate on your advice for managing the “millennial mindset?”

There are so many generalizations about millennials in today’s workplace, but at the end of the day they need to be managed as individuals with different needs, strengths, and weaknesses. One thing that I can say is that millennials pushed brands to be more transparent, so sharing as much as possible about the inner-workings of the company is a great way to build trust (one of our core values). This satisfies everyone’s curiosity about company performance, while also instilling a greater sense of individual value and responsibility. But at the end of the day, treat everyone fairly and equally regardless of generation and associated stereotypes.

What are your “5 Ways to Improve Your Company’s Culture” and why. (Please share a story or example for each.)

a. Have an internal, company-wide plan that includes goals and methodology for teams and individual employees. Marc Benioff originally coined the V2MOM (an action plan based on “Vision, Values, Methods, Obstacles and Measures”) for doing so, which is something that I took with me from my time at Salesforce and still use for my team today.

b. Hold your employees accountable for results. Having access and visibility into your individual, team and company-level V2MOM plans makes this more achievable. A culture of accountability creates that needed trust and respect.

c. Have fun in the right way. It’s especially important to plan time for your employees to celebrate milestones together. Make sure that these celebrations are inclusive, as you are winning as a team; that means that even if it’s a huge sales number that’s being celebrated, other teams that contributed to the success even indirectly — such as product, customer success and marketing — should still be included.

d. Encourage a round-the-clock “pay it forward” mindset. Dedicating work hours towards employee volunteering is great, but paying it forward should be an everyday occurrence. That includes being appreciative and regularly showing gratitude towards peers and supporting staff who allow everyone to succeed both personally and as a team.

e. Celebrate diversity. It’s not enough to source and hire a diverse team: the team as a whole can benefit by learning from different cultures and perspectives. If you have an overseas office, encourage both offices to celebrate each others’ holidays and heritage.

Strong company culture is something that everyone likes to think they have but very few have it. Why do so many organizations struggle with creating strong, healthy work environments?

There are a few buzzwords that companies like to incorporate into their mission and values. Yet it should be a bottom-up approach of assessing what values already exist within your team, and how to mix that with achievable, “inspirational” values to strive towards. Be honest about who you are and what you do. This should apply to the company road map — you need to have an aggressive but achievable plan in place so that your team hits milestones and feels great about it.

What is one mistake you see a young start-up founders make in their culture or leadership practices?

A mistake that I often see is young founders who aren’t realistic about what they know and don’t know. They should be honest with themselves about their strengths and stick to those, and hire people who are really experienced and trustworthy to fill in the gaps. Learn and listen to the experts in their respective fields.

To add to the previous question, young CEOs often have a lot of pressure to perform and often wear many hats. What’s a simple time efficient strategy they can start doing today to improve their company’s culture?

Be 100% sure that you are hiring the right HR team and then trust those individuals to do their jobs. Make sure they understand and are aligned with where you want the company to go in terms of people and culture, and let them carry out your mission for you.

Don’t blindly follow VC-based recommendations as VCs are not there for the day-to-day and do not understand every intricacy of your organization’s culture.They tend to make suggestions based off of what they’ve seen at “similar” companies that may or may not be applicable. On that note, it’s helpful to have an independent board member that will back up you and your goals.

Success leaves clues. What has been your biggest influence in your leadership strategy and company culture? Please feel free to share a person, book, another company, etc.

The person who has had the biggest influence on my leadership strategy is my father. His motto was to “be tough, fair and just.” This strategy has helped shape some big decisions over the years and has always served me well.

What advice do you have for employees that have bad bosses? How can they take control and improve a bad situation?

The course of action is so dependent on the circumstance, but if it’s in regards to work-related issues and expectations, it’s important to ask your boss to be clear and open about his or her workload and priorities. If there is a disconnect, it’s important to isolate it in order to work towards a solution. The next step might be having a skip level meeting with your boss’ manager. This manager may need insight into the daily workings and expectations of your team in order to help align those broader expectations, and will hopefully be able to remedy the situation from there.

However if your boss is violating policies on company conduct, this should be directly reported to the head of HR and the CEO. Going straight to the most senior employees within the company offers protection from retaliation. If the CEO is involved, go to the board. No one should be afraid to go all the way up the chain for workplace violations.

Okay, we made it! Last question — what’s one unique thing (hack) you or your company does that has enhanced your work culture?

As mentioned earlier, we really value celebrating diversity and having fun. At Helpshift, we have large teams in both San Francisco and Pune, India — so celebrating and embracing our differing heritage is ingrained in our culture. For example, last year the Pune team had a “Secret Santa” party and this year the SF team will celebrate Diwali!

Originally published at

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