When we were trying to move upmarket at Pave, I made 5 deadly mistakes that caused me (and the company) massive growing pains: 𝟏. 𝐈 𝐭𝐫𝐢𝐞𝐝 𝐠𝐨𝐢𝐧𝐠 𝐮𝐩𝐦𝐚𝐫𝐤𝐞𝐭 𝐛𝐞𝐟𝐨𝐫𝐞 𝐨𝐮𝐫 𝐑&𝐃 𝐚𝐧𝐝 𝐂𝐒 𝐭𝐞𝐚𝐦𝐬 𝐰𝐞𝐫𝐞 𝐫𝐞𝐚𝐝𝐲. Moving upmarket isn't just a sales thing. It's a COMPANY thing. You need dedicated engineering support. You need enterprise CSMs who are ready to go all in on a 3 month implementation. Or you end up with churn. 𝟐. 𝐈 𝐭𝐫𝐢𝐞𝐝 𝐠𝐨𝐢𝐧𝐠 𝐮𝐩𝐦𝐚𝐫𝐤𝐞𝐭 𝐰𝐡𝐞𝐧 𝐭𝐡𝐞 𝐩𝐫𝐨𝐝𝐮𝐜𝐭 𝐰𝐚𝐬𝐧'𝐭 𝐫𝐞𝐚𝐝𝐲. You can scope as much as you want, but the reality is that you NEVER have it all scoped in enterprise sales. If you're still battling potholes in your core product, bringing on an ENT customer will only rip those wider and expose new ones. 𝟑. 𝐈 𝐝𝐢𝐝𝐧'𝐭 𝐫𝐞𝐚𝐥𝐢𝐳𝐞 𝐭𝐡𝐚𝐭 𝐠𝐨𝐢𝐧𝐠 𝐮𝐩 𝐦𝐞𝐚𝐧𝐭 𝐬𝐥𝐨𝐰𝐢𝐧𝐠 𝐝𝐨𝐰𝐧 𝐩𝐫𝐨𝐝𝐮𝐜𝐭 𝐞𝐯𝐞𝐫𝐲𝐰𝐡𝐞𝐫𝐞 𝐞𝐥𝐬𝐞. When you get pulled by a potential $250k churn, they derail your entire product roadmap. The one big deal hurts your win rates and product velocity everywhere else. 𝟒. 𝐌𝐨𝐯𝐢𝐧𝐠 𝐦𝐲 𝐛𝐞𝐬𝐭 𝐬𝐞𝐥𝐥𝐞𝐫𝐬 𝐨𝐟𝐟 𝐭𝐡𝐞 𝐜𝐨𝐫𝐞 𝐨𝐟 𝐭𝐡𝐞 𝐓𝐀𝐌 𝐰𝐢𝐭𝐡 𝐭𝐡𝐞 𝐛𝐞𝐬𝐭 𝐏𝐌𝐅. Bigger deals do not mean more ARR. I promoted my #1 seller who did $750k in a QUARTER in the mid-market. She did $400-500k in her *best* quarter in ENT and had to work 10x harder for every dollar. *** I've learned a lot about the right time to move upmarket and how to do it. Selling 6 and 7-figure deals is a blast. But it can also sink your company. And I'm sharing the battle scars with my good friend Jason Bay tomorrow :) Join us live --> https://hubs.ly/Q02GzjJT0
Absolutely! At Habit10X, we help teams navigate market shifts and scale effectively. Studies show 60% of companies face major setbacks when scaling without aligning R&D and CS teams (Source: Harvard Business Review). It's crucial to understand that shifting markets can expose and amplify existing issues, and overestimating your team's ability to handle larger deals often leads to burnout and misalignment. Our Accountability Partner Program helps ensure you're ready for these transitions by addressing gaps and aligning strategies.
Moving before product is ready can be dangerous, but sometimes it's required to get product moving faster. How do you strike that balance?
Looking forward to it Armand Farrokh!
CEO @ InsideSalesExpert.com Helping sales leaders avoid galactically ridiculous mistakes in all areas of building, fixing & growing their sales teams
4moWhen we were first attempting to "go up market" at ZIP back in 2013-2015, it was a disaster for several of the reasons above with a notable difference: - We weren't willing to build out the Enterprise product at all instead focusing all of our product and engineering resources on our core product, SMB. This was the smart thing for the company to do with limited resources but the mistake was thinking that we could sell to Enterprise level companies with our same SMB product merely by hiring some "Enterprise salespeople." Thereafter, when somebody would ask me "what's my Enterprise sales strategy?" I'd reply "You tell me what our Enterprise product strategy and our Enterprise marketing strategy is and I'll develop you a kick@$$ Enterprise sales strategy." When you go up market to go after Enterprise companies, you win as a company or you lose as a company. As you said, it's not just a sales issue.