HR Tech Interview with Leslie Pendergrast, Chief People Officer at Outreach

Leslie Pendergrast recently joined the Outreach team as their Chief People Officer. In this chat with TecHRseries, she takes us through her HR journey and biggest takeaways through the years while sharing a few thoughts on today’s evolving talent management trends.


Tell us a little about yourself Leslie…and your journey through HR. You’ve recently taken over as Chief People Officer of Outreach; can you tell us about some of the biggest plans you have? 

Scaling tech companies is a passion of mine.  While it’s stressful during the building process, it’s so rewarding to look back and be part of a team that has positively impacted the organization and business success.

Today, I’m focused on:

  • Diversity, Equity and Inclusion: Outreach is already focused on creating a more inclusive environment.  We will continue this work and build out a more holistic strategy that will include diversity hiring, ensuring our practices are fair and unbiased, community involvement, and inclusion in the workplace.  We view DE&I as integral to all of our People pillars.
  • Creating a leadership framework: Fundamentally, everyone plays a leadership role at Outreach, regardless of where they might sit on the org chart.  This framework will create the intentional expectations of how we work together, including getting it done and doing it right. Once we have this framework articulated it will be the basis of our people practices including hiring, performance assessments, hiring, training and development, and more.
  • Building a top-notch virtual work experience: We’re introducting new wellness applications, coordinated time off and employee pulse checking. In the new year, we will launch a new employee engagement survey to determine, with more specificity, where we can do a better job of supporting our employees’ success, which will inform our plans.

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From your time within HR in tech, while building people practices: what are some of the biggest takeaways you’ve gathered?  

My top three takeaways are:

  • People practices have to authentically match the culture as they will drive how people behave. It’s critical that you are intentional about your values and expected behaviors, so that you can build practices that support them.
  • Practices should be guidelines and allow for flexibility in different locations and departments. Assume positive intent and build practices for the 99% of people who seek to do things right.
  • Policies should only be written when you need to follow legal or compliance related matters.

As today’s talent market and workforce adjusts to the norms of the new normal, how are you seeing trends shift in hiring and talent acquisition in B2B / Tech? 

Watching this unfold is really interesting. The response to the new normal is varied.  While some believe productivity has declined, others think it has improved.  To me, it’s varied based on the role, the team and the leader.  I know leaders who have sworn by an office presence, but are now rethinking their approach.  This situation has provided an opportunity for leaders to question their paradigms.  Many companies have declared they will remain remote going forward, others are still taking a wait and see approach.  Regardless, it opens up the ability to expand the net of our talent pool.

Seeing how business leaders had to rapidly pivot to adjust to the challenges the Covid-19 pandemic brought on, what do you think are the biggest concerns for HR globally today? And how would you address them? 

Of course, the safety of employees is top of mind, both physically and psychologically.  We can’t be complacent in the continuous monitoring of our employees’ well-being.  People across the globe are in different phases of the pandemic. It’s a cycle of highs and lows, emotionally.  One of the most important we can do is continue to monitor through frequent check-ins and manager meetings. We need to offer solutions based on the needs of the employee or the team.  It’s not a one size fits all.

Another interesting challenge is the current job market.  When COVID-19 first hit, the initial thought was preservation of employment.  We were all bracing for the worst and thought the job market would be, at a minimum, stagnant.  But this has turned out to be a very competitive market, especially in the tech space.  Many companies are hiring and you have to offer a compelling, holistic story to candidates, inclusive of compensation, flexibility and the ability to make a difference.

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What should companies keep in mind now, given the norms of the new normal, while resetting company policies and employee practices?  

If you didn’t have flexible, employee friendly practices, it has now become a requirement. Trust people to do their jobs. Assume positive intent and assess performance based on outcomes vs. face time.

How do you feel HR can play a bigger role during this time to ensure businesses are productive and have adequate resources? 

The current working environment has elevated the role of HR. Emotional struggles, working from home and meeting burnout are all real challenges right now. I believe the best practices are still the same, but they must be more frequent, more consistent and more intentional.

Communication and caring are key components of success. We need to think through how to improve our 1 to 1 meetings, coaching and feedback, performance reviews, engagement surveys, etc. to ensure that these practices are holistic and focus on the whole person vs. just the work outcomes.

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As young tech companies and their teams expand globally, what are some of the basic best practices they should follow to inculcate an employee friendly work policy and culture? 

Ensure that you have values and people principles that align with your culture. Hold people accountable and use them as a foundation for your practices.

A few parting tips on what companies and HR heads should keep in mind as they shape their strategies in 2021 amid the new normal?

You don’t always know what’s going on at home for your employees, especially now – enable flexible work schedules, while showing trust. Assume that they will still put in the time to produce their best work, even though you no longer have line of sight to their workspace. When an employer shows they care, so will the employees.


The Outreach Sales Engagement Platform helps efficiently and effectively engage prospects to drive more pipeline and close more deals.

Leslie Pendergrast is the Chief People Officer at Outreach

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