Today we are talking to Craig, the SVP of Engineering at SendGrid.  And we discuss advice to CTOs going through a merger or acquisition, winning over the team by solving the problems that really matter, and why as a leader, the most important thing you can do is bring in the next generation of leaders.

All of this, right here, right now, on the Modern CTO Podcast!

Craig brings over 15 years experience leading, contributing to, and growing engineering organizations in top SaaS technology companies. Craig joined SendGrid in early 2015 from Cisco where as the Senior Engineering Director, he most recently grew the organization from a small co-located startup to a team of 150 distributed engineers.

In his 7 years at Cisco, Craig held multiple Senior Engineering roles across Mobility, Platform, and Messaging focusing on growth and scale while modernizing architectures and processes. Prior to its acquisition by Cisco, Craig successfully grew from Technical Lead to VP of Engineering for Jabber where he was responsible for all of engineering – client (both desktop and mobility), server, and quality assurance.


  • Joel is a big fan of SendGrid – Founders Isaac Tim and Jose were part of the first Techstars class.  First Techstars program to go public
  • Has over 80000 customers using SendGrid
  • How did you get to SendGrid?  Was at a big company, Cisco for a long time.  Wanted to get to something smaller
  • The amount of resources that are out there for people to learn from is amazing
  • What’s your biggest lesson as you became a first time leader.  Needed to wear his big boy pants to work every single day. Biggest mistake was around configuration UI for a tech product.
  • What’s your leadership style as a whole? Varies based on stage of company.  Early stages it’s hands on benevolent dictator. As it grows it becomes a lot more coach mentor.  These days it involves next generation leaders.
  • Example of working around the rules and challenging the process.  Encourage him to take the next step and work with different teams to
  • Let people who are passionate and competent take risks
  • Tiger teams – pulling a few people from different teams that are highly skilled and putting them together in isolation so they can make heads down progress. Internal think tank not a Craigism
  • When you pull a tiger team together they get something that is mission critical.  When they are successful it’s easy to give them accolades. Have an award that they give out – ghost tiger award – most value least drama
  • Advice to CTOs in merger or acquisition.  There is so much opportunity for folks if it’s a good fit.  Led engineering at Jabber and was acquired by Cisco. Get to see your baby grow up and be wildly successful.
  • Has also seen through acquisition where sales director was tapped to lead the product organization.  Today he is GM for mobility and automation group. Opportunity that never would have been there within a small company.
  • SendGrid / Twilio acquisition lets both companies realize their dreams.
  • So much opportunity if the acquisition has been well vetted.  Many fail because of poor vetting up front
  • On the revenue side SendGrid was growing north of 30%. In engineering they have doubled in headcount from 80 to 170 and will be 200 in the next quarter
  • Are you hands on involved with talent acquisition? How do you set up your talent pipeline?
  • Great book called the first 90 days.
  • Not much that you do as a leader that’s more important than bringing in the next generation of leaders and making sure you get that right.  Put more on the burden on the hiring managers shoulders. Have very effective recruiters who can source talent and do screening. Needed to step up on the ownership from the engineering managers side.  What that looks like is putting together a very clear job desc. Finding ideal candidates on Linkedin.
  • Engineers are much more likely to respond to a engineering leader than to a recruiter.  Expects them to go look where recruiters aren’t expected to make much headway
  • First 90 days – first 30 is analysis – next is situational.  Manage up. Set expectations. Everything is on fire. These are the top 3 things that we’re going to address.  Taking the time to build the comprehensive plan. Not reactive, strategic instead.
  • Winning over a team, naval admiral taking over a carrier.  The morale of the troops was in the toilet. As he took time to analyze problems, the thing they hated most was the fact that they had to strip the paint off the boat and repaint it every single year.
  • What is innovation to you?  Agrees that innovation is small improvements over time.  Innovation shows up in process, tooling, in how you lead.  Not just about product innovation.
  • Thinks about the product world on horizons.  Horizon 1 is transactional email.
  • Second is the next business that they will launch.  Horizon 3 is a a labs program. Has a formal process around how they validate that what they create is something the world would actually want.
  • How do you run labs? Historically as a completely separate team. Recently they have made the decision to redistribute that. Labs group will now embed in to a number of engineering teams so that they can do this in greater scale.
  • What are you most excited about today?  The merger between SendGrid and Twilio. Getting it right to realize the combined vision. Customers don’t want 2 bills, they want a platform that provides insights that are independent of channel.
  • There’s a lot of change and there are a few people who get excited about change.  That’s not the normal reaction. Doing it in a way that people can wake up excited
  • Drives a Tesla – has to be a fan in some way.  Spends a lot of time thinking outside of the box. There’s a reason they are there
  • What piece of advice would you give yourself?  It took him forever to figure out not to separate business and personal.  It’s okay to have personal relationships with people and be your authentic self. Appreciate people for their authentic selves. Listen better. Admire in leaders who he respects is that they are generally good human beings first.

Joel Beasley

Joel Beasley founded the Modern CTO Podcast in 2017 while writing his book, the Modern CTO book, with the goal of interviewing CTOs and sharing their experiences with others in the tech community.

Joel’s conversational style and insightful questions quickly gained traction, attracting high-profile guests such as Microsoft’s CTO, Kevin Scott, and T-Mobile’s CIO, Cody Stanford. With each episode, the podcast’s popularity continued to grow, and soon, Joel found himself with a waiting list of future guests.

Today, the Modern CTO Podcast has become the number one leadership and tech podcast in the world, with over 150k active listeners, including CTOs, lead developers, and rising tech leaders. Joel’s commitment to creating a conversational atmosphere for his guests to share their experiences has inspired a new generation of leaders and innovators.

As the success of the podcast grew, Joel founded ProSeries Media, a podcast production company that helps companies worldwide create their own podcasts. With a team of producers, content creators, and podcast bookers, ProSeries Media produces over ten shows, providing a platform for companies to connect with their audience and share their expertise.

Through his work on the Modern CTO Podcast and ProSeries Media, Joel Beasley has become a respected voice in the tech industry, inspiring others to share their knowledge and insights with the wider community. His passion for creating engaging content that informs, inspires, and entertains has made him a sought-after speaker and advisor on all things tech.

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