Why I Built an AI Sales Coach (After 20 Years of Selling)

There's a pattern in sales technology: engineers identify a problem, build a solution, and then hire salespeople to explain it. The result? Tools that look great in demos but collect dust after the first month. I built Opsight because I've been on the other side of that equation for two decades—and I was tired of tools that didn't understand what it's actually like to sell.

The Fear Everyone's Talking About

Let's address the elephant in the room. Bloomberg research suggests AI could automate 67% of sales rep tasks. Forbes Advisor found that 77% of workers are concerned about AI-driven job loss.

I get it. The anxiety is real. But here's what that research misses: the same Salesforce data shows that 68% of sales teams using AI actually added headcount last year, compared to only 47% of teams without AI.

AI isn't replacing salespeople. It's replacing salespeople who don't adapt. There's a difference.

Why Most AI Sales Tools Fail

BCG research shows that 74% of companies struggle to achieve value from their AI investments. In sales specifically, adoption often stalls at 30-40% because of three problems:

1. The Black Box Problem: AI spits out a score or recommendation with no explanation. When it doesn't match your field experience, trust evaporates.
2. Limited Context: The tool doesn't understand your deal, your buyer, your industry. Generic advice is useless advice.
3. Built by Engineers: The people designing the algorithms have never had a quota breathing down their neck at month-end.

I've used these tools. I've watched my reps ignore them. And I've sat in vendor demos thinking, "This person has never made a cold call in their life."

The Mentor Who Changed Everything

Early in my corporate career, I was assigned my first official mentor. He was an experienced sales leader who had spent decades crafting his methods. He didn't just teach me tactics—he taught me a system.

• Pipeline management—not just this quarter, but the next three quarters
• Follow-up cadence—disciplined, consistent, systematic
• Sales personalities—how to adapt to different buyers
• The "why" behind each stage—not just what to do, but why it works

That mentorship revealed every mistake I'd made building a B2B team by myself with no playbook. I started documenting everything. That mentor—now retired for almost a decade—still advises me regularly. He was even one of Opsight's beta testers.

But here's what I also learned: most reps never get that mentor. Not because good mentors don't exist, but because:

• Not many reps ask for mentorship
• Not many companies cultivate this culture
• Not many leaders have the willingness or time to invest

The reps who get great mentors accelerate their careers. The rest figure it out through trial, error, and lost deals.

The Frustration That Started Opsight

As a manager, I'd sit in 1:1 meetings with my reps, staring at dashboards showing 100+ metrics. I could see what was broken—low activity, stalled deals, missed quotas.

But I had no idea how to fix it.

The data was there. The direction wasn't. I could see my reps struggling with the same objections, making the same mistakes week after week. But I couldn't be there for every call, every deal, every moment of doubt.

That's when the question hit me: What if every rep could have a mentor like mine? Not once. Every day.

Built Different: What Makes This Personal

I didn't outsource this to a dev shop. I didn't hire a team of engineers to build what I described. Over two years of nights and weekends, I built Opsight myself—using the same coding skills I'd developed as a teenager tutoring students in C++ back in India, combined with AI assistance that let me put my entire process into code.

What went into it:

• 287+ sales books I'd read over my career, synthesized into the NOVA-6 methodology
• 20+ years of field experience—wireless retail, B2B, enterprise tech
• Five semesters teaching Sales & Sales Management as an adjunct professor
• The actual systems that made me a top performer year after year

I restarted the project four times after thinking I'd reached launch. There were nights I thought about giving up. But I kept going because I knew the pain I was solving was real—I'd lived it.

AI as Partner, Not Replacement

Here's my philosophy, and it's baked into every line of code: The user is the coach. We're just the assistant coach.

AI isn't here to replace your judgment. It's here to:

• Surface the signals you'd miss across 50 deals
• Remind you of the methodology when you're tempted to skip steps
• Give you the "why" behind each recommendation so you can decide
• Adapt to your personality—because a High-D doesn't want the same coaching as a High-S

I'm still a top performer at my day job. AI hasn't replaced me. It's made me more consistent, more systematic, and better at catching deals before they go dark.

The Trust Problem—And How We Solve It

Remember those three reasons AI tools fail? Here's how we address each:

1. No More Black Boxes

Every health score shows exactly how it was calculated. Every recommendation explains the "why." If the AI says a deal is at risk, you can see the specific signals: days since last activity, stage velocity compared to average, methodology gaps in your notes.

2. Your Context, Not Generic Advice

Opsight reads your actual deal data—not some abstract model of what deals "should" look like. The coaching adapts to your pipeline, your stage definitions, your sales cycle. It learns your patterns and flags when something doesn't match.

3. Built by Someone Who Sells

This is the hardest one to replicate. You can't fake 20 years of quota-carrying experience. You can't fake teaching Sales & Sales Management to students. You can't fake the frustration of sitting in 1:1s with nothing actionable to say.

Every feature in Opsight exists because I needed it. The "Today's Most Valuable Actions" feature? Born from research showing reps face 200+ decisions every Monday morning—I reduced that to 3 per deal. The DISC-adapted coaching? Because I watched the same feedback land completely differently depending on the rep's personality.

Who This Is For

If you're looking for AI to do your selling for you, this isn't it.

Opsight is for:

• Reps who want to improve but don't have access to great mentorship
• Managers who are overwhelmed with data but starving for direction
• Leaders who want consistency without micromanaging
• Teams doing more with less after layoffs hit

We're priced at $49/month for individuals and $69/user for teams because everyone deserves access to world-class coaching methodology—not just enterprise companies with six-figure enablement budgets.

The Bottom Line

AI in sales has a trust problem. Tools built by engineers who've never sold don't understand what reps actually need. Black-box algorithms that can't explain themselves get ignored. Generic advice that doesn't fit your deals wastes everyone's time.

I built Opsight because I wanted the tool I wished existed when I was building that first B2B team with no playbook. When I was staring at dashboards with no idea how to coach my reps. When I was trying to be the mentor I'd been lucky enough to have—but for everyone on my team, every day, at scale.

The 17-year-old who walked a mile to work in the rain. The manager who built a B2B team alone. The adjunct professor. The top performer. They're all the same person. And they built this because everyone deserves the mentor that changed his trajectory.