Jamal Reimer’s Post

Playing it safe in enterprise sales? That’s how you stay forgettable. If you want to close deals, you have to master familiarity and novelty - at the same time. Most sales reps play copycat. They talk the same, pitch the same. It’s what they teach you, it’s safe, it builds trust And puts them to sleep and gets your number blocked. Your clients are flooded with reps saying the same thing. Be predictable, and they’ll skip right past you. But hit them with something unexpected, And now, they’re paying attention. Mirror their language to get them comfortable, Then drop in a unique, valuable insight That only you can see and provide And speaks direct to them. Familiarity will keep them listening; Novelty makes them want more. What You Actually Do (WYAD) Be ready to stand out, and ditch the safe script. Sell with fresh ideas in familiar packaging And proven ideas in shiny new boxes. ————————————— House of Sales Learn.Sell.Grow. ————————————— P.S. My newsletter went out late, apologies, it is on the site now - www.b2bhouseofsales.com

Lots of good Enterprise Sales tips and strategies outlined here, but I thought I’d add one more of my own: Enterprise sales is personal. What I mean by that is, it's crucial to remember that the decision-making process often happens at the ground level. Customers choose partners based on personal interactions and the value they feel is brought to their specific need. Our role in enterprise sales is therefore twofold: First create those personal connections then provide a service that complements the other technologies and services the customer already trusts. https://hubs.li/Q02M1wcj0

Here is a great take from the fine folks at Zendesk sharing what Enterprise sales is REALLY all about. It's a great resource I want you to read and keep as a reference. It is full of solid learnings and best practices. If you are a Founder with no sales background, or you are new to Enterprise sales, this article will impact your sales beliefs and best practices going forward.

Enterprise Sales: Unleashing True Potential Through Listening" In enterprise sales' fast-paced, competitive day-to-day, one undervalued skill is Active Listening. But here's the game changer—it isn't just about courtesy; it's about transforming your complex sales process through a deep respect for your client's input. When you genuinely listen, you're sending a powerful message to your enterprise-level prospects: "Your business goals matter. Your complex challenges are valid. I'm willing to invest time to understand and align with your strategic objectives.

Closing a successful enterprise deal requires patience, persistence, and diligent follow-up. Did you know that 80% of sales require 5 follow-up calls after the meeting and that 44% of sales reps give up after just one follow-up attempt? These stats prove that consistent and proper follow-up is critical for enterprise sales success. By mastering strategic follow-up, you can set yourself apart and build the relationships needed to close complex, high-value deals. Don't leave this crucial piece of the sales process to chance. Implement a structured cadence and leverage technology to help track and manage your outreach. Aim for 5-12 meaningful touches over time through calls, emails, and in-person meetings. Stay top of mind while providing value - share insights, new developments, and anything that will help contacts achieve their goals. The difference between winning and losing in enterprise sales boils down to one thing - diligent follow-up. Proper follow-up turns prospects into customers and sets you up for continued success. Make it a cornerstone of your sales strategy and secure your spot at the top.

I talked to an 'enterprise salesperson' last week that told me his company changes the sales territories every year. It’s one of the dumbest things a company can do. A true enterprise sale often takes 18-36 months. By playing musical chairs with nominated accounts, they are going to yank the salesperson out of the territory just as they are getting traction... ...and give the opportunity to someone new that the prospect doesn't know or trust. If there are any Execs of SaaS vendors out there, please PLEASE don't allow this to happen. You're just sabotaging your own success. Create a key account plan, identify any traction within the account, provide support where needed and BE PATIENT. There are ways to measure early traction beyond hard revenue. If you can't hold your nerve longer than 6 months, then you shouldn't be trying to do enterprise sales in the first place. Am I wrong?

Founders, don't build your enterprise sales motion before validating that the problem is critical to your customer’s success. If you have something that works in a different market don't assume it will be easy to lift and shift into enterprise. It has its own nuances. You need to understand what drives urgency for these unique customers and how your solution fits into their strategic priorities. And it’s not enough to talk to just one customer — you need to gather insights from multiple buyers who share the same use case. Lead your sales process with the knowledge you’ve gathered from your research phase. Position yourself as an expert in their world. Show them you understand their burning problem. Tell them they're not alone and that you're hearing the same problems from their peers. Highlight the value your solution delivers for them by referencing what your research (read:customer) conversations. If you can build trust and establish yourself as an expert upfront, it will earn you the right to do discovery and tailor your pitch to their needs, reinforcing the idea that you're a trusted advisor who deeply understands your customer.

When I first started doing enterprise sales, I would follow up consistently and still get 0 responses. After closing multiple enterprise deals so far this year, with a few more this month coming into the pipeline, I finally found the solution: I was contacting uninterested prospects. As a result, they saw me as spam. The solution? Focusing on my ICP and adjusting my messages to address their pain points. Enterprise sales rarely result from a single touchpoint. Prospects don't respond to your first cold outreach - which makes following up extremely important. What should you follow up with? - New product features or improvements - Similar customer case studies - Industry insights and trends - Prospect-specific news (e.g., funding, key hires, product launches) Learn from my mistakes: - Focus on your ICP and target your messages to address their pain - Show how your solution can solve their top-priority problems and add value - Be helpful and relevant, not pushy or intrusive A well-timed follow-up can generate 5-figure opportunities for your business. This lesson has been a game-changer for our sales at Relate.