Challenges of trust in SMB software adoption

"If you are still here in 12 months, let's talk" When growing a SaaS product from 0 to 10, this objection came up daily in sales meetings with SMB owners. It infuriated me. At the time, I didn't have the perspective or reps in the tank to understand this and, more importantly, move into deeper discovery. Behind this line was a single core reason I was getting pushed back. Trust. After some upskilling and knowing how to peel back this objection, I learnt each SMB owner had: 1. Been burnt before by another vendor 2. Seen people enter and leave their market multiple times 3. Were not going to risk their stable business on a new market entrant Here are the 3 approaches I used to open up the discussion and peel back the real reason: 1. "Typically when I hear this from business owners like yourself its because 1 of 3 reasons"... Why it works: Social proof lets them steer the conversation to a key point: you have brought forward the problems. 2. "Look, it's a little unusual, but we are a new business and getting raw feedback on this would be super helpful for me, what's the reason behind the reason here? Be as blunt as possible." Why it works: It's refreshing and shows you aren't here to just get a sale you want to make it in their industry. People naturally want to help. 3. "Fair enough, even if I were to come back in 12 months, what would need to have changed for you to go, 'Sean, looks great, congrats on making it 12 months, let's do this". Why it works: You aren't fighting the objection and are instead putting them into a future state mindset of perfect world, this creates more opportunity for discovery once they explain what they need to see. Often this is where the trust conversation came up and can created a branch to partner this prospect until they were comfortable and trust was built. Finally, as a business, we focused on building trust in the market by: 1. Develop case studies and strong customer testimonials 2. Being visible in industry conferences, EDM's, Associations 3. Building micro commits in the buyers journey process validated by proof of delivery This whole post is a reminder business is about the long game. Hearing “if you’re still here in 12 months” is a great opportunity to put yourself in the shoes of the customer and remember every objection is a chance to build trust, refine your approach, and strengthen relationships. In the long game, that’s how you win. What’s the toughest objection you’ve faced—and how did you handle it?

Buying technology is easy. Getting people to use it? That’s the hard part. Too often, companies invest in new software expecting it to transform operations overnight—only to hit major roadblocks with operational alignment and adoption. The system gets underutilized, workarounds emerge, and the promised efficiencies never materialize. Sound familiar? Here’s why technology adoption stalls: ❌ Poor process alignment – If tech doesn’t fit how people actually work, they won’t use it. ❌ Lack of user buy-in – People resist change when they don’t see the value. ❌ Insufficient training – A one-time demo isn’t enough. Users need hands-on learning and job aids aligned to their day-to-day activities. ❌ No accountability – Without clear expectations and leadership support, adoption suffers. A successful implementation isn’t just about turning the system on—it’s about making sure people actually use it. That’s why a change management strategy is essential to drive adoption and long-term success. When we help clients select and implement new vendor management systems, we focus on more than just system setup—we develop a change strategy to drive adoption. This includes: ✅ Setting clear adoption goals and success metrics to measure impact and progress. ✅ Engaging users early to gather requirements and build buy-in from the start. ✅ Optimizing workflows to ensure processes align with and fully leverage the technology. ✅ Designing tailored training, support, and feedback mechanisms to reinforce adoption. ✅ Ensuring leadership actively supports and champions the change to drive accountability. Technology alone doesn’t drive change—people do. Investing in adoption strategy is just as important as investing in the software itself. What’s been your biggest challenge with technology adoption? Drop a comment below! ⬇️

"Everybody thinks it gets easier when you’re at $100M+ ARR, cash-flow positive, and growing. But I just had the worst two months of my entire life.” That’s what Marcelo Lombardo, founder of Omie, told me on Friday. Omie is the Brazilian SaaS giant founded in 2013. They just announced a $160M Series D. With 180K SMB clients and 30-40% annual growth, they’re the #1 cloud ERP and fintech for small businesses in Brazil. They are real OGs in the BR ecosystem. I picked Marcelo's brain on his learnings going from $0 to $100M ARR. "It doesn't get easier as you grow, it just gets different". I burst into nervous laugh but also in relief. The conversation was so fun and full of golden nuggets that deserve to be shared.. so here are some of the lessons and stories he shared: 1. Borrow credibility to open doors In the early days, he picked up the phone relentlessly to speak with his first customers and ask a simple question: “Do you remember where you found us?” Many said “Google", until he pressed. The real answer: “My accountant told me to use Omie.” That’s when they realized accountants, not ads, were the real channel. They flipped strategy into partnerships with them. Today they drive 80% of Omie’s sales. 2. Commissions can erode trust “If my client finds out I’m making money from this, it hurts my credibility. Give them the discount instead.” the accountants would tell him. The best accountants valued trust over margin. Incentives that work in SaaS backfire when partners are fiduciaries. 3. Trust lowers walls faster than incentives When Marcelo asked accountants if he could sell to their clients directly, they handed him their entire client list. Why? “Because they trusted me.” he said. Alignment matters more than commissions. 4. Trust scales through presence “The job to be done is not to scale software sales, but to scale trust.” Omie’s AEs visit 3-4 accountants a day, every 15 days. Not to pitch, but to listen: “What’s your problem today? What’s your client’s pain?” That cadence compounds relationships and yields warm intros. 5. Trust is long-term leverage Instead of outspending competitors on ads, Omie built a distribution moat by being the most trusted partner to accountants. Other nuggets from our call: - Trust > commissions - Give partners the product for free so they become power users - Keep partnerships alive with cadence: 3–4 visits/day - Great partners protect client trust; weak ones chase margin - At every stage, the problems change, but trust is always the multiplier If you're building a compay, or operating, I encourage you to share what you learn, you never know who you help. Shoot me a comment or a dm. Now, back to building 💪. #startups