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Office Hours: I’m Shailvi Wakhlu, former Head of Data from Strava. I recently published a book on ‘Self-Advocacy’. AMA!Featured

Hi Elphas!

I’m Shailvi Wakhlu, a soloprenuer, author, and the former Head of Data & Analytics at Strava and Komodo Health. Salesforce and Fitbit are the two other significant companies I worked at.

I started off my career journey as a Software Engineer. I eventually made my way to analytics and also ran my own startup building apps more than a decade ago. This past year was my ‘year of exploration’, as I quit my tech job to write my book and became a first-time self-published author. I was already doing 25+ yearly speaking engagements on Data and Self-Advocacy, and this year, I began doing corporate engagements with companies who want to bring self-advocacy expertise to their ERGs. Additionally, I became an Angel Investor with a Data syndicate investing in Data companies, and also created/instructed data courses for multiple online platforms.

During my downtime, I enjoy traveling and have visited 32 countries. Currently, I live in SF and have no plans to ever leave. I grew up in India as an army-kid, and being outdoors and in nature feels like home. I love plants and my apartment has 60+ plants on the last count. My husband and I met in college, have been together for decades, and are child-free by choice.

Ask me anything about leading global analytics & engineering teams, strategy, improving business efficiency, influencing through “data storytelling”, becoming a keynote speaker and an author, or anything else!

Thanks so much for joining us @shailvi!Elphas – please ask @shailvi your questions before Friday, December 8th. @shailvi may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕
Thank you so much for hosting me! This was fun and the questions were great. I'd love to stay connected with this community and am looking forward to getting to hear everyone else's stories as well!I tried to answer the most popular/oldest questions first. Didn't get to all of them but hopefully I provided some resources for the ones where I was unable to give detailed answers.Thanks everyone :)
Hi Shailvi! Thanks for making the time! How exciting to have had a "year of exploration". I'd love to hear more about this decision and what you have discovered this past year :) Is it the first time you take a year to do something like this?
Thanks Josefina!Yes this was my first time doing this, and after a 16 yr career I felt I had earned some time for exploration :) Plus I really wanted to publish my book - so it was also taking time to do that intentionally, and making sure while I was at it I tried other things as well.One fun thing I discovered in the past year - I can gamify all my life goals and don't have a problem with self-motivation :D I'd love to have given a more detailed answer but my office hours are up. Feel free to connect on LinkedIn!
Fascinating! I will take you up on connecting over LI :D
Hi Shailvi,Thanks for this wonderful post. I can relate as I am too an Indian+army kid product, so far visited 7 countries and counting and no kids as well(so far) :D I carved my path in data analytics and now I am building data products. I have 12+ years of experience. As you can understand it takes endless nights and a lot of hard work to do what you really want and ultimately carve your own career trajectory by going against the traditional career routes. And again these steps are always an ongoing action item for a person like me because you are always evolving the best version of yourself. Here are couple of questions from my end to you I would love to hear your thoughts:1. Have you ever had any mentors to help you mold your career path? If yes, then where were your mentors most impactful?2. I do believe in data story telling too. But how to navigate in an organization who don't believe in storytelling at all and are not even open to learn from their peers. Have you ever been in this situation?
Thanks Harshita and I appreciate the questions!1. I didn't have any formal mentors for most of my career, though I had many great bosses and people who were a little ahead of me in their career who volunteered help and advice along the way. In hindsight, I really wish I had sought formal mentors, and proactively cultivated those relationships to help me with specific challenges I faced. I think mentorship is most helpful when the expectations on both sides are clear. I had an executive coach for 3 out of the last 4 years, and it was a relationship I really benefited from. I chose someone who I had good chemistry with, and who was willing to challenge me when I needed it. It helped me specifically through two different job transitions, and many challenging situations at work. Their objectivity since it wasn't someone I reported to was helpful. As was the fact that they were an expert at coaching, and not just doing me a favor over lunch was valuable to me as well.2. Yes, unfortunately :) There are companies who say they want to be data-driven / data-informed, but aren't always willing to put resources, time, or a commitment behind that mindset. I truly feel any data practitioner's job is as much about people, as it is about data. Data can give you a great insight, but it is people who need to act on it. Data can show you a revolutionary business result, but it is people who have to be convinced to do something different. My best advice is to focus on the motivation of individuals, especially people who are decision-makers on how data insights will be actioned. Don't focus on the best story you want to tell, but on the best story that gets specific people to do something that is better for the business. Aligning your storytelling tactics with that goal in mind, tends to yield better results. Good luck!
Hi Shailvi, Thank you for doing this question and answer session. You have done many awesome things. Congrats on the book! It is inspiring.You have traveled globally what are your thoughts on the convergence of consumer data, generative AI, and ethical issues. It seems as though US is taking a lead in creating some dynamic conversations between Big Tech and government in dealing with emerging issues. Is there more that needs to be done? What can we do in our leadership roles day to day to help society in this emerging issues? My thoughts are a certain level of cybersecurity traing coupled with ethics training may be a starting point.Which countries had the best salad, tea, and coffee that you traveled to? Any opinions which country has the fastest mobile internet and best performing cell phone hardware?In my experience, it appears to be countries in far east, but I have seen some advance usages of digital currency in certain African countries. Digital currency has changed the landscape a little.Thank you for doing this! Have a great holiday season.Lisa
Thank you Lisa!Consumer data, gen AI and ethical issues are bound to collide. I think inevitably the focus will become on 'what's in it for me' for the consumers, and ethical concerns have to reach some sort of a stable point. I actually believe Europe will lead the way in some of the legal expectations, as they are quicker to reach consensus on these topics and actually enforce them. US of course has the capacity to create the platforms where this is actively discussed, but right now in gen AI the monetization still has some question marks, and people are more focused on that. So yes, more needs to be done before we ignore a problem that gets too big to tackle. On a daily basis leaders need to be intentional about what they are putting out, and make sure to establish some best practices that are expected in every single part of the data lifecycle. Cybresecurity and ethical training are good ideas! Data quality training should be included as well.Tea (herbal) - TurkeySalad - DenmarkCoffee - I don't drink coffee :)I don't know about all the countries and their mobile / internet situation, but I have always been impressed with India especially when I compare it to US and Europe. It's cheap, reliable, and very quick innovation. I'm biased though since I go to India more often than any other country outside of US.
Hi @shailvi, I'm a startup founder in the data-based health analytics space - could you talk a bit about how big consumer apps like Strava and Fitbit prioritize their R&D strategy and how much they do in-house vs through API licensing? Any insights you have into how they prioritize new tech and partnerships would be greatly appreciated!
Hi Alexandra,I'd love to give a more detailed answer, but unfortunately my office hours are up. Some of your questions are not something I can disclose about my ex-employers, to maintain confidentiality. For other insights let's connect on LinkedIn, I often post about similar insights especially about how startups think and execute on these things.
Hi Shailvi, Thank you so much for introducing yourself and sharing part of your story! I have a few questions for you:Can you share a pivotal moment in your career that led you to decide to quit your tech job and pursue writing your book as a self-published author?Can you share a memorable experience from your travels that had a significant impact on your personal or professional development?As someone who advocates for self-advocacy, what strategies do you recommend for individuals, especially those in tech, to assert themselves and navigate their careers effectively?
You have had and continue to have such an amazing career at some of my favourite companies/products (Strava & Fitbit) doing such important work! How did you get started with the idea of writing a book and why this topic in particular? Also what was the process of being self-published?
Thanks Iynna! I'm glad my background resonated :) I wrote this book based on a talk I gave 4.5 yrs - "How to #HumbleBrag Effectively". At the time, it was a topic I was thinking a lot about myself, and it felt cathartic to talk about it publicly. The first conference I spoke at had a packed 100-person audience for my topic, and I realized how much people cared about this. I iterated on the topic many times and spoke about it for the next 4 yrs, and I also mentored 350+ people. Eventually, it reached a point where I figured I should take all the knowledge and put it in a book format, for a wider reach.Self-publishing was a fun process - though I am not an expert. I had planned to traditionally publish, until I spoke to a bunch of authors and realized all the pitfalls of that process which wouldn't have worked for my situation. Broadly speaking, you can think of self-publishing through the construction analogy: a) you can DIY and do all the editing, designing, marketing, etc yourself, or b) you can hire individual experts for the pieces, or c) you can find the equivalent of a general contractor, who works with you to build what you want. I went the (c) route and it worked well for me. Through self-publishing I get to keep more royalties, had a fast time-to-market, had a lot of control over my final product, and I own the IP of my work which is how I can still do paid speaking engagements based on my book.
What would be your top 3 advice for someone early in their leadership role? How does the role change as one grows ? What would be 3 to look out for in a company which can be detrimental/ pull you back?
Great questions Chinmayi!1. What would be your top 3 advice for someone early in their leadership role?My top 3 pieces of advice:a) Read the book 'The first 90 days'. I think it helps you think about your role in a structured way, and provides many useful playbooks for how to clock in early wins.b) Find people who are willing to mentor you in this transition. I would ideally suggest at least 1 of these mentors should be outside your company, and if you are in a large company then one of your mentors should be within your company. The person outside your company should ideally be someone you can see yourself maintaining a relationship with for many years.c) Don't be afraid to ask questions or ask for help. Leaders are not expected to have all the answers, but they are expected to not be fazed by the unknown and go solve for it.2. How does the role change as one grows ?As you grow in a leadership role, you should get more comfortable handling complexity, ambiguity, and trying things you don't know. I personally feel one of the biggest causes of stagnancy or lack of growth for a leader is their tendency to only play to their strengths and not try things they aren't good at yet.As you grow, the people challenges also tend to get more complex, as do business challenges. You have to be prepared to make tough decisions, and lead with conviction. One common example relevant from the current market is layoffs - no leader ever becomes one hoping they'd have to take away jobs one day, but you have to have the stomach to do it when it is needed, prevent it as much as possible, and thoughtful execute it with compassion and kindness if it's inevitable.3. What would be 3 to look out for in a company which can be detrimental/ pull you back?My top 3 red flags to look for:a) Leadership misalignment. If leaders above you are meaningfully misaligned in what the company does and what it should do, chaos and bad execution are inevitable, and will eventually hurt your career in some way. b) Bad business sense. I no longer work for companies that are only interested in making shiny products, that are "cool" but "unsellable". If people don't want to pay for a product, you don't have a business. If a company does not know or is not interested in finding the path to profitability and growth, your career can only grow till they grow.c) Values misalignment. I've been very fortunate to work for companies where the values felt aligned. I've turned down jobs where despite the money, I knew I'd hesitate when the misaligned values were apparent. It's I think a key thing to look for when joining a company / team.
Thank you so much for your reply @shailvi This is helpful to navigate and plan.
Did you always know you wanted to be child free? If not, how did you come to this conclusion?
Great question Kathryn!I did not. I had always assumed I would have kids, but I wouldn't say I was ever dreaming about kids either. It just felt like the default thing to do. It was after a few years of being married that my husband and I realized that neither of us actually wanted to have biological kids, for many personal reasons. We sat on it for a few years, to make sure we both felt 100% sure of that decision, especially since culturally it's an unpopular decision. Tomorrow we celebrate our 12th wedding anniversary and 19 yrs of being together, and we have been sure it's the right decision for us for a long time now :)
Thank you for sharing this story! You're so introspective and that has really served you. "I had always assumed I would have kids" assume is the key word here, like is this what you want or what the world wants you to do .. !
Thank you for sharing!
@shailvi- thanks for sharing your knowledge and wisdom. You are my next point B and where I want to go- aka become an author and a speaker. Can you share your 0-1 launch of your book - where you began, any resources you recommend for someone with a goal to write a book in next 12 months? did you self-publish? how did you find editor? if you can share the whole lifecycle i would really appreciate it
That's great Shradha! I'd love to give a more detailed answer but my office hours are up. If you connect with me on LinkedIn I often post about my speaker and author journey. I have a webinar I will run soon about speaker process and that will answer a lot of the questions you have.For the author stuff - I am a first time author and I self-published. I posted a video during my book launch which answers some of the questions you asked: https://www.youtube.com/watch?v=33WNgEGy2OM (description should allow you to skip to the relevant section).Good luck!