Introducing Luck Dookchitra, new Leapsome VP People

In these times of diverse workplace challenges, strong People leadership matters more than ever. At Leapsome, people enablement is part of our DNA, and nothing is more important to us than fostering employee development, productivity, and engaging work environments. We want to ensure that we live and breathe these principles, not only in working with our customers but in our own HR processes as well. Therefore, we had to find a really special person to lead our People and HR work as we steer our company — and hopefully the whole industry — into the future of work. 

That’s why we’re so excited to have Luck Dookchitra join the team as our new VP People. Luck has a rich and impressive resume, heading up People efforts at well-known companies like Spotify, Teachable, Modern Meadow, and Troop HR. She’s also done amazing work as a certified professional coach and advisor to new businesses. 

We sat down with Luck to talk about her incredible career so far, her philosophy on People and Culture, and her plans for the future at Leapsome. This isn’t just a “hello” to Luck; it’s a sneak peek at the kind of strong, people-focused leadership she’s bringing to our company and our industry.
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“I hope to bring calm during periods of change or uncertainty. I hope I can bring insight into our customers and what we need from products as HR leaders. I hope I can bring mentorship to enable my own team as well as others throughout the organization. I hope I can connect us more deeply into the HR community across the US, and I hope we continue to make Leapsome an amazing place to work. I hope that all employees at Leapsome feel engaged and supported during their time here and that we continue to progress toward this audacious mission our founders have set — joyfully, together.”

— Luck Dookchitra, new VP People at Leapsome

What does running a People team mean now and into 2024? 

Luck — The world of work is rapidly changing, and the role of a People team is more important than ever. These days, it means predicting the future in a lot of ways — anticipating what global or local events might trigger employee discourse or distraction, considering which new tools and trends to utilize, determining what’s reactive vs. right, and balancing employee needs and business realities with heart, humanity, and the bottom line. 

The role of the People team has evolved dramatically in the last decade, largely thanks to technology advancements and the increasing demands from new generations entering the workforce. Through these evolutions, the People team has become responsible for growth, development, guidance, connection, engagement, education, awareness, well-being, diversity, equity, inclusion, belonging, accessibility, justice, and ultimately, business success and impact for leaders, employees, and investors alike.

Nowadays, the table stakes for a strong People function go well beyond policy, payroll, and benefits. People teams must enable high-performing cultures and must bring the employer value proposition to life in ways that attract both customers as well as current and future employees while also satisfying investors and public reaction. In recent years, all of this has been quite the juggling act, especially for under-resourced People teams, who continue to get more “to-do’s” on their list, often based on the latest trends. 

Yet, People functions are often the first to be asked to trim budgets or are seen as cost centers themselves — while still retaining the expectations to serve in all of the ways listed above. 

Running a People team now and into 2024 and beyond requires resilience, balance, strength, and heart. People teams must do the following to succeed:

1. Demand resources and convince leaders to prioritize these needs and deprioritize others since the work of the People team serves the full employee experience. 
2. Create bold strategies to test out new ways of working and advocate for what is right for both the people and the business.
3. Remember the fundamental cornerstone of HR — caring for humans and delivering through kindness. 

As we move into a new quarter and a new year, we can only expect one constant: change. People teams are on the frontline of every current event and new trend or social media sensation; every market swing in either direction, every new workplace debate about burnout, 4-day workweeks, the return to the office, salary transparency, and more. 

We must be ready to respond with thoughtfulness in communication and actions where warranted. We must bring calm to chaos and illuminate where things are unclear. We must serve as a caring coach for our CEOs, our C-suite, our managers, and all of our employees.

In the future of HR, the People function continues to be a strategic partner to the business that is highly integrated into company performance and no longer seen as just a support and administrative function. Well-supported People functions and teams will result in better business results, deeper engagement, high employee enablement, and happy customers. 
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How has the world of HR changed in your career so far?

Luck — I’ve been working for over 20 years and focused on HR and People and Culture work for over 15 of those. It has been a wonderfully transformative and expansive period in this field. I was fortunate enough to land my first HR roles within very progressive companies that were people-first, meaning that investing in People and Culture was a priority. I believe this shift in workplaces to care about their employees has been a crucial driving factor in making the HR function what it is today. 

New markets of technologies, services, and goods have been created as a direct response to the demands employees have of their workplaces and leaders, and People functions are at the center of driving these emerging markets. The People Executive role is now an integral part of a complete leadership team — responsible for important initiatives that sustain business results and drive culture — not just the policy police. 

I’ve been happy to see that investments are being made into the People function. When I began my career, it was normal to have just one HR employee, and that team of one was hired too late. Now, we invest in headcount and budget for People teams, and they are called upon to be more fully integrated into functional teams as HRBPs, and are charged with driving learning and engagement as a priority versus an afterthought. 

It’s exciting to see the transformation both within companies internally as well as in the market landscape. There are countless (and growing) numbers of tools serving HR work processes now, whereas, in my early days, I was primarily using Excel and Google Sheets! I can’t wait to see what new tools we’ll see in the coming years and what new roles and responsibilities we take on as the future of work unfolds.

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What is the biggest learning of your career so far? 

Luck — The biggest learning in my career is to prioritize your own well-being. Having worked at countless high-paced startups during periods of tremendous growth and change, it’s easy to get caught up in work. I’ve been lucky in that I’ve always enjoyed diving in. 

However, as my own life events happened, like getting married and having children, I learned that you can’t work at the same pace. I often feel tremendously guilty about not being able to give 100% to either world. But I’ve come to learn that you can’t give anything if you don’t put on your own oxygen mask first. To me, this has been setting clear boundaries about where to get involved and making sure that I make time to fill my own cup. It’s been about making time to read, learn, and explore hobbies and to spend uninterrupted time with my kids or on a topic of interest (either work- or life-related). 

I’m sparked by deep work, creating, and innovation, so I find outlets to do this kind of thinking and tinkering in work and life in order to feel fully energized. I’ve learned that without prioritizing these aspects, burnout is not too far behind. The recovery time from burnout is much longer than anyone thinks. It also takes a lot away from you. Burnout is a tricky thief in that it comes subtly — taking a little bit from you over time but leaving you utterly drained, disengaged, and unmotivated. A massage or week off usually doesn’t cure it. It takes thoughtful and intentional work to get back to normal. 

Just as we engage in preventive checkups at the dentist and during our annual medical visits, preventative mental health requires automated check-ins with ourselves and our teams to ensure we remain balanced. We acknowledge there will be times of rigor, but we must also balance it on the whole with meaningful pauses.
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How do you, as a People leader, define success? 

Luck — Success for me, personally, is living by my values and remaining in balance. It means providing services that make work more meaningful and providing growth opportunities to my team in ways that catalyze their careers. 

Success for a People function is being so deeply integrated that we can provide a second brain and thought partnership on important human and business-related matters. It means that we help the organization and its people — at all levels — to weather growth, change, and life in ways that still support the company’s bottom line. It means we feel aptly rewarded for our work and our time in total rewards, health, and well-being. It means still feeling inspired by our day-to-day work and excited about tomorrow’s work, too.
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What is the one thing you think is crucial for all People leaders to know right now? 

Luck — People leaders, no matter where you are in your career, take a moment to appreciate and recognize your many contributions and gifts. Please take time to pause, fill your own cup, and reconnect with what sparks and motivates you. In our work, we hold space for others in many ways that aren’t typically defined in a skills matrix or job description. This work still matters, and YOU and your unique approach to all things People-related matters. Put your oxygen mask on first — at least sometimes!
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What does a good company culture look like to you? Why Leapsome? 

Luck — A good company culture means engaged employees who are excited about the mission. It means that employees are able to find ways to grow and learn and continue to stretch throughout their tenure — and it means a culture of employees who are problem solvers versus problem finders.

It means leaders who listen and remain curious and who aren’t afraid to admit to mistakes; managers who have tough but caring conversations when necessary and who talk about the hard things as well as the good and great things.

It also means customers who are thought partners because they stick with us, help us develop the latest innovations and thereby help us grow while we help them build great cultures and connections.

It means celebrating each other and feeling connected — even across geographic and time zone differences. It means that every employee feels like they belong.

Why Leapsome? Well, what a dream opportunity! A global company whose mission is to make work fulfilling for everyone based on an incredibly powerful technology platform and with a team of people across all functions who care about how and why we work — sign me up! 

In addition, the founders, Jenny and Kajetan, have a strong vision and deeply care about the people, the product, the customers, and the state of the business. They’ve made prudent choices to set up Leapsome for scale and growth.

And, like anyone else, I wanted to find a role where my expertise could be utilized while further growing myself in different ways. In this role, I come with deep expertise in US/North American HR operations as well as global high-growth experience in the SaaS technology space, but I am eager to become more ingrained in the global People leader community and partner more deeply with Product, Engineering, Marketing, Sales, and Customer Success as a target customer. 

I’m also incredibly excited to work with the People & Culture team, who laid an amazing foundation for Leapsome’s great culture and have been incredibly welcoming and supportive in my onboarding. I want to extend a special shoutout to my two team leaders, Claire and Kate:

Claire Rosenthal was Leapsome’s first employee, and I feel so fortunate that she can continue to help us shape the future of Leapsome and lead us in defining what people enablement means tangibly for our employees and leaders. Kate Arsova, who joined just under a year ago and has already helped us navigate incredible global growth while finding amazing talent as we continue to grow in Germany and New York, is now helping us scale and structure our People operations practices across continents.

The full team is so impressive in their passion for innovation, people enablement, and the deep care and consideration they have for our employees — I feel lucky to be inheriting such an amazing team. Even beyond my own team, since Leapsome is in the business of directly supporting HR teams and forward-thinking business leaders, every team member from Customer Success Coach to Head of Finance to Product Manager to Software Engineer, is working on the stuff that matters deeply to employees everywhere, and I can’t wait to get to work!

“Leading a People function is a great privilege and a big responsibility in serving our colleagues in ways that can make work fulfilling for everyone.”

— Luck Dookchitra, new VP People at Leapsome

Outlook

As we wrap up our discussion with Luck, it’s clear that her arrival marks a pivotal chapter for Leapsome. Her depth of experience and dynamic approach to leadership are exactly what’s needed as we navigate these complex times. With Luck at the helm of People & Culture, we’re not just welcoming a new VP; we’re embracing a vision that aligns perfectly with our core values and aspirations. As we move forward, under Luck’s guidance, we’re not only anticipating significant growth for our team but also an invigorating push toward redefining industry standards. So, this isn’t just a conclusion to a conversation, it’s the commencement of an exciting, people-centric journey at Leapsome. Stay tuned — there’s much more to come.

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