Shashank Saxena

MANAGING PARTNER

Shashank is a Managing Partner at Sierra Ventures, where he leads enterprise software investments. Before Sierra, Shashank was the Co-Founder and CEO of VNDLY, which was founded in 2017 as a Vendor Management System (VMS) in Cincinnati, OH, and acquired by Workday in 2021 for $510M.

After the acquisition, Shashank was the General Manager for Workday VNDLY.

Shashank started his career in IT applications management in banking, retail, and e-commerce before building a successful track record at Fortune 25 companies, such as Citi and Kroger, Co., where he led corporate strategy and digital transformation.

Shashank has also been an active early-stage angel investor and venture partner and has been involved with multiple other SaaS companies.

Shashank has a bachelor’s in computer science, a Master of Business Administration in finance, and a Master of Science degree in information systems from the University of Cincinnati.

Insights from Shashank

What are the top three things you think about when looking at a potential investment?

1. Founder/s - given most of our investments are early stage, the bet is largely on the founder. Certain personality traits I tend to focus on are - do they add clarity or create confusion? Have they demonstrated past ability to overcome hardships in their personal or professional life? Any prior examples of “delayed gratification” is a huge bonus.

2. Headwinds and tailwinds - where are the macro trends in the industry, category or vertical headed towards? Will these macro trends benefit a tenacious founder?

3. Focus and alignment - is this truly a problem worth solving? We’re in the business of providing capital and expertise, so our alignment with the problem area is critical and proportionate to the value we'll add to the entrepreneur's journey.

What advice do you have for founders?

1. Be a fantastic human being - this makes it very easy for employees, customers, partners and investors to align with you on your journey

2. Understand the product really well - this helps build and maintain trust and competence

3. Good leaders never disconnect from the front lines - as organizations scale, this becomes even more important to not lose touch with the customer pain points

If you had to recommend one book to an entrepreneur what would it be?

Zero to One by Peter Thiel

What is your best “life-hack”?

Non-rushed mornings - for the past 10+ years, I’ve tried to start my day in a non-rushed manner. 8 hours of sleep, a morning workout at least thrice a week, no work meetings before 9 am - all set the tone for mental calmness and a relaxed state of mind that lead to clarity of thought and mindfulness.