Enterprise Sales - Lessons From 1000+ Client Calls
Today’s advice post is by Dan Lesley, Founder of Homestar. Dan has over 20 years building, growing, and selling SaaS tech startups.
Having built Homestar from scratch and navigated countless enterprise deals, I’ve learned that enterprise sales is far more nuanced than I initially imagined. The early days were rough - I remember staring at my laptop before major calls, heart racing, wondering if our CRM could really compete with established players in the real estate space.
The reality of selling to enterprises hit hard when we first started pitching Homestar. Between coding sprints and team meetings, I found myself diving deep into the peculiar world of corporate buying cycles. Some days felt like speaking a foreign language, especially when explaining our CRM’s value proposition to stakeholders who’d been using legacy systems for decades.
Active listening became my secret weapon. Instead of launching into rehearsed feature demonstrations, I started asking about their pain points. During one memorable call with a major brokerage firm, their IT director spent 20 minutes venting about their current system’s shortcomings. That conversation completely reshaped our product roadmap.
The enterprise ecosystem surprised me with its complexity. Each stakeholder brings their own agenda to the table. Technical teams scrutinize integration capabilities, finance folks dissect pricing models, and end-users worry about learning curves. I learned this lesson the hard way after a promising deal fell through because we hadn’t adequately addressed security team concerns.
Company culture blindsided me more than once. A potential client in the Midwest seemed perfect on paper - they needed what we offered. But their risk-averse culture clashed with our agile approach. Now I spend hours researching organizational values before important meetings.
Trust-building takes time in enterprise sales. Some of our best clients took months of consistent follow-ups, sharing industry insights, and proving our reliability. One client signed after nine months of relationship building - worth every coffee meeting and status update.
Setting realistic expectations became crucial after a few early mishaps. During one implementation, we discovered our API couldn’t handle their custom workflows. Now I’m upfront about limitations and timeline constraints. Clients appreciate this transparency, even if it means longer sales cycles.
The relationships we’ve built extend far beyond initial deals. Our first enterprise client still calls me directly with feedback, and their success stories have opened doors to other opportunities. These connections have proven invaluable as we’ve scaled Homestar.
Market awareness shapes every conversation. Real estate tech evolves rapidly, and staying current helps anticipate client needs. When iBuyers disrupted the market, we quickly adapted our platform to help agencies compete.
Key lessons from thousands of enterprise interactions:
- Listen deeply to uncover unstated needs and concerns
- Map your solution to each stakeholder’s specific objectives
- Research and respect organizational culture
- Build trust through consistent, valuable interactions
- Set clear expectations about capabilities and timelines
- Maintain strong relationships post-sale
- Stay ahead of industry trends and adapt so
Enterprise sales fundamentally comes down to human connection. Technical specs matter, but trust and understanding drive decisions. After years of pitching Homestar, I’ve found that authentic relationships lead to the most successful implementations.
The enterprise sales process reminds me of orchestrating a complex performance where timing, preparation, and execution all matter. Each deal teaches something new about business relationships and human nature.
Looking back at countless pitches and implementations, these experiences continue shaping how we approach enterprise sales at Homestar. The journey’s been challenging but incredibly rewarding, especially seeing how our solution helps real estate professionals succeed.