Why Getting to Know Your Competitor CEOs Is Your Secret Weapon
The counterintuitive relationship strategy that could transform your business
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5 Reasons to Meet Your Competitor’s CEO
- They could buy you someday (or vice versa) – 60% of B2B exits involve industry consolidation. Personal relationships turn cold M&A processes into strategic partnerships.
- De-escalates later tensions – When conflicts arise, having a direct relationship prevents destructive price wars and allows for respectful competition that benefits everyone.
- Helps you focus on the bigger prize – Competitor insights reveal market opportunities you can’t see from your perspective alone, expanding your strategic vision beyond daily battles.
- Share a little, learn a little – Strategic information exchange about market trends and ecosystem developments makes both companies smarter without compromising competitive position.
- Creates unexpected opportunities – From joint market education initiatives to ecosystem partnerships, relationships open doors that pure competition cannot.
Your biggest competitor today might be your one of your bigger opportunities tomorrow. While conventional wisdom says to keep your enemies close, smart CEOs take it a step further—they get to know their competitor CEOs personally. Not just professionally. Actually know them.
I’ve seen this play out dozens of times across hundreds of portfolio companies. The CEOs who build genuine relationships with their competitors consistently outperform those who don’t. Here’s why this counterintuitive strategy works, and how to do it right.
One Of You Might Buy The Other … Someday
Let’s start with the numbers. In the enterprise software space, roughly 60% of successful exits involve some form of industry consolidation. That means there’s a better-than-even chance that your biggest competitor today becomes your acquirer tomorrow—or vice versa.
Consider the Salesforce ecosystem. Marc Benioff didn’t just compete with companies like ExactTarget, Pardot, and MuleSoft. He got to know their CEOs personally. When acquisition conversations began, these weren’t cold corporate transactions—they were discussions between people who understood each other’s vision and values. The same pattern played out with Slack—despite being fierce competitors in enterprise collaboration, the personal relationship between leadership teams enabled a $27.7 billion acquisition that transformed both companies. The result? Some of the most successful SaaS acquisitions in history.
Cisco’s $28 billion acquisition of Splunk in 2024—the largest tech transaction of that year—was built on years of partnership and mutual respect between the companies’ leadership teams. When CEO Chuck Robbins and Splunk’s Gary Steele discussed combining networking infrastructure with observability platforms, they weren’t strangers negotiating across a table—they were industry veterans who understood each other’s strategic vision.
This isn’t just about being acquisition-ready. It’s about positioning yourself strategically for whatever comes next. When you know the person across the table, you understand their motivations, their constraints, and their real priorities. That intelligence becomes invaluable whether you’re buying, selling, or just trying to coexist.
The De-escalation Dividend
Competition in B2B can get nasty fast. Price wars, talent poaching, customer badmouthing. But CEOs who know each other personally rarely engage in mutually destructive behavior.
When you’ve had dinner with someone’s family, it’s harder to justify carpet-bombing their pricing strategy. When you understand their personal journey and struggles, you’re less likely to engage in the kind of scorched-earth tactics that hurt everyone.
This doesn’t mean being soft or avoiding competition. It means being smart about how you compete. When tensions arise—and they will—having a direct line to resolve issues before they escalate saves time, money, and reputation for everyone involved.
Focus on the Bigger Prize
Perhaps most importantly, knowing your competitor CEOs helps you see the forest for the trees. When you’re deep in the trenches of daily competition, it’s easy to lose sight of the bigger market opportunity. Personal relationships with competitors provide perspective you can’t get anywhere else.
Your competitor CEO sees the same market dynamics you do, but from a different angle. They’re hearing different customer pain points, seeing different adoption patterns, and identifying different growth vectors. When you can have honest conversations about these observations, you both get smarter about the real opportunity.
The Information Exchange
The key to making competitor relationships work is establishing the right information-sharing protocol. This isn’t about sharing customer lists or pricing strategies. It’s about exchanging market insights that help everyone understand the broader landscape.
Here’s what smart CEOs share:
- Market size observations: What are you seeing in terms of overall market growth? Are enterprises increasing budgets in your category?
- Competitive landscape insights: Who are the real threats coming up from below? What technologies are customers asking about?
- Ecosystem developments: How are the big platforms evolving? What partnership opportunities are emerging?
- Talent market intelligence: What compensation trends are you seeing? Which recruiting strategies are working?
The rule is simple: share information that helps both companies understand the market better, but never share anything that could directly harm your competitive position.
How to Actually Do This
Building relationships with competitor CEOs requires intentionality and the right approach. Here’s the playbook:
- Start with industry events. Conferences, roundtables, and industry dinners provide natural opportunities for initial contact. Don’t pitch or position—just be genuinely curious about their journey and perspective.
- Suggest coffee or dinner. Once you’ve established initial rapport, suggest meeting outside of industry events. The goal is to move beyond surface-level networking to actual relationship building.
- Be genuinely helpful. Share insights that benefit them without directly hurting you. Make introductions to relevant contacts. Offer perspectives on challenges they’re facing.
- Establish boundaries early. Be clear about what you will and won’t discuss. This transparency builds trust and prevents awkward situations.
- Focus on the person, not just the business. Ask about their background, their motivation for starting the company, their vision for the industry. Understanding their personal story helps you understand their business decisions.
- Meet regularly. Relationships require maintenance. Quarterly dinners or monthly coffee chats help maintain connection and provide ongoing market intelligence.
The Risks and How to Mitigate Them
This strategy isn’t without risks. The biggest concern is information leakage—accidentally sharing something that gives your competitor an advantage. Here’s how to minimize this risk:
- Prepare for conversations. Before meeting with a competitor CEO, think through what you’re comfortable discussing and what’s off-limits.
- Focus on industry-level insights. Talk about market trends, not specific customer situations or internal strategies.
- Avoid operational details. Don’t discuss pricing strategies, sales processes, or product roadmaps.
- Trust but verify. Pay attention to whether information you share shows up in their messaging or strategy. If it does, adjust your sharing accordingly.
- Get legal guidance. Have your legal team review any formal information-sharing agreements or joint initiatives.
The Long Game
Building relationships with competitor CEOs is a long-term strategy that pays dividends in unexpected ways. The CEO you have dinner with today might become your acquisition partner in three years. The market insights you exchange might help you both identify a new category opportunity. The mutual respect you build might prevent a destructive price war that would hurt both companies.
In the fast-moving world of SaaS, it’s tempting to view every other company as an enemy to be defeated. But the most successful CEOs understand that markets are big enough for multiple winners, and that understanding your competitors as people—not just businesses—creates opportunities that pure competition cannot.
Your competitors aren’t just obstacles to overcome. They’re fellow travelers on the entrepreneurial journey, facing many of the same challenges you are. Getting to know them personally doesn’t make you soft—it makes you smart. In a world where information is power, having honest relationships with the people who see the market from different angles gives you a strategic advantage that no amount of funding or features can match.
10 Tech Deals Where Competitors Became Partners
The M&A reality isn’t theoretical—it’s happening constantly across tech sectors. Here are five major deals where fierce competitors ended up in the same company:
1. Salesforce + MuleSoft ($6.5B, 2018) – Two companies competing in the enterprise integration space, where Salesforce needed MuleSoft’s API connectivity platform to compete with Microsoft and others.
2. Microsoft + LinkedIn ($26.2B, 2016) – Microsoft and LinkedIn weren’t direct competitors, but both were fighting for enterprise mindshare. The acquisition gave Microsoft a social professional network to compete with Google and Facebook’s enterprise offerings.
3. Adobe + Marketo ($4.75B, 2018) – Direct competitors in marketing automation, where Adobe needed Marketo’s B2B capabilities to complete its marketing cloud and better compete with Salesforce.
4. Workday + Adaptive Insights ($1.55B, 2018) – Workday acquired its planning and analytics competitor to enhance its financial management suite and better compete with Oracle and SAP.
5. Splunk + Phantom ($350M, 2018) – Two cybersecurity companies competing in different but adjacent spaces—Splunk’s data analytics platform acquired Phantom’s security orchestration technology to create a more comprehensive security offering.
6. Slack + Quip ($750M, 2016) – Before Slack acquired Quip, both were competing for workplace collaboration mindshare. Salesforce later acquired both companies separately, showing how competitive relationships can evolve through multiple transactions.
7. Zoom + Keybase ($50M+, 2020) – As video conferencing exploded, Zoom acquired end-to-end encryption competitor Keybase to enhance security capabilities and better compete with Microsoft Teams and others.
8. Okta + Auth0 ($6.5B, 2021) – Two identity management platforms that competed directly for developer and enterprise customers, with Okta acquiring Auth0 to strengthen its developer-focused offerings.
9. Twilio + SendGrid ($3B, 2018) – Competing communication platforms where Twilio acquired SendGrid’s email capabilities to build a more comprehensive customer engagement platform.
10.Cisco + Splunk ($28B, 2024) – This was the largest tech transaction of 2024, where Cisco acquired cybersecurity and data analytics competitor Splunk CiscoInvestopedia to combine networking infrastructure with observability capabilities and create a comprehensive AI-powered security platform.
The question isn’t whether you should get to know your competitor CEOs. The question is: can you afford not to?
