The Sales Playbook That Turbocharged Outreach from $0 to $200M ARR
Our November NY Enterprise Tech Meetup focused on a topic we’re particularly passionate about at Work-Bench: enterprise sales and go-to-market tactics.
After just a few years on the job, most CIOs will typically have heard ~100 sales pitches. And 7x CIO Mark Settle has heard the good, the bad, and the ugly.
While there’s no magic formula for an effective sales pitch, over his tenure vetting and purchasing software from startups, along with many conversations with fellow CIOs and technology buyers, Mark’s developed a proven method for startups to efficiently define their value and close the deal.
Before diving into Mark’s “formula,” it’s important to understand that while CIOs may be senior gatekeepers to a company’s technology budget, they’re by no means the only gatekeepers. Traditional top-down sales is commonly thought of as the preferred strategy to collapse the sales cycle. If you “wow” the CIO, most of your hard work is done. However, this is also a high-stakes, calculated risk because if you’re unable to garner the CIO’s enthusiasm off the bat, your campaign could be dead in the water. But nowadays, many stakeholders (including the end user…hello PLG) are involved in the decision to invest in new technology and different VPs hold their own budget authority.
For those who have decided the CIO is the right sales entry point, here is a recap of Mark’s top tactics as well as a recording of his webinar on the topic.
While booking a meeting with a CIO may sound easy, Mark confessed that sending a cold email is a challenging and often failed approach in breaking through the noise of the CIO’s busy inbox. Instead, look for warm inroads - aka a recommendation from another CIO, trusted VC, or respected member of the company’s IT team. In that initial outreach, you should include:
Note: If a cold email is your only option, make sure it is extremely well researched and personalized. Do not copy and paste generic messaging from previous pitches.
With most meetings lasting just 30 to 60 minutes,* Mark warned not to follow Alec Baldwin’s famous advice to “always be closing.” Instead, focus this precious time on booking a second meeting, not closing the deal. To do that, he recommends following these five rules:
*Note: 30 minutes minus 5 minutes if the CIO arrives late minus 5 minutes for introductions minus 5 minutes to determine next steps = 15 minutes or less to actually engage the CIO.
What do vendors typically want to know?
What do CIOs typically want to know?
Never assume the CIO has been pre-briefed on your meeting. Instead, quickly establish context and relevance before diving into more specific product information.
Don’t waste time:
Ensure there’s enough time for a thoughtful conversation about ‘next steps’ at the end of the meeting.
If there’s a specific request for additional information or follow up activities, make an explicit commitment as to when that will be done and report the completion of those requests/activities after they’ve occurred. If there’s no explicit request, ask for a homework assignment or preemptively commit to certain actions based upon the conversation.
Happy selling!
If you’re thinking about launching an enterprise software or SaaS startup or have already taken the leap, it's never too early to connect with us. We’d love to meet you to learn more about what you’re building, share our best feedback, and plug you into our enterprise community where helpful.