Suggestions
Taylor Grabus
Vice President of Sales Global @ Datadog
Taylor Grabus is a sales leader currently serving as Vice President of Sales at Datadog, specializing in mid-market sales across North America, EMEA, and LATAM regions.1
Professional Background
Career Progression at Datadog::
- Current Role: Vice President, Mid-Market Sales (March 2023 - Present)
- Previously served as Senior Director of Mid-Market Sales (September 2021 - March 2023)
- Director of Mid-Market Sales for North America and Commercial LATAM (August 2018 - September 2021)
- Started as Sales Manager and Enterprise Account Executive at the company1
Key Achievements::
- Launched Mid-Market sales segment in EMEA market
- Created a new sales segment focusing on companies with 1,000 - 5,000 employees
- Helped Datadog through its IPO in 20191
Prior Experience::
- Enterprise Account Executive at Datto, Inc. (June 2016 - January 2018)
- Earned Presidents Club honors in 2015 and 20171
Professional Philosophy
Taylor is passionate about sales leadership and team development. He emphasizes the importance of outbound pipeline generation and believes in meaningful coaching through top-of-funnel metrics.3 He particularly values sales deals where his team's success is the primary focus.2
Highlights
If you are in sales, stop asking the question "how does this (pain) effect your business?"
Not using this question doesn't mean it isn't important to uncover the business implications of a prospects technical pain but more over that there is way more effective way to get to the answer.
Part of becoming a strategic/consultative seller requires you to have a deep understanding of the businesses you work with. Starting with the knowledge of how your customer business model works (how they make money), how they are leveraging technology/people to execute on that model (what is the true utility of the resources) and the strategic plan for how they want to advance their organization.
With understanding the above you can then take preliminary technical pain and begin to hypothesize up-stream implications on the business. Instead of the generic "so how does this (pain) impact your business?" take the opportunity to show that you understand your customer's model and help lead them to potential metrics that are tied to their specific organization.
Happy selling people!
I have an absolute passion for sales but my favorite deals as a leader are the ones that I had very little to do with....
I pride myself on being a sales leader that knows whichever product I am selling and the struggles that come along with it. Sounds simple but I can think plenty of my own experiences where leaders have spent 95% of their time driving the business from dashboard or on the reverse side of it where leaders are carrying 95% of the deal.
As scope widens I have to make a consistent effort to make sure this part of me is not lost. I think similarly to the age old balance for an AE of managing sizable pipeline while still prioritizing net new business prospecting.
I will say this though, there is nothing better than winning a strategic deal that I had little involvement with. We can always qualify more and provide coaching but watching a seller grow their skillset to become close to autonomous is incredibly gratifying. Jumping into a deal review, prep call or customer meeting and leaving it with confidence that exceptional work is being done is unmatched.
Creating repeatable process, driving accountability on expectations and not being afraid to roll the sleeves up. Happy selling folks!
