1. Too Many Stakeholders, Too Many Opinions

The problem: You don’t just sell to one person. You sell to a squad. And no one tells you who’s actually in charge.

The fix: Use AI to map influence and track stakeholder engagement.

Tools that help:

• Gong – Tracks stakeholder talk time and patterns across calls.
• People.ai – Maps buyer groups and shows you who’s influencing deals behind the scenes.
• Tenali AI – Automatically identifies which stakeholders ask the toughest questions and helps you tailor your responses live.

Why it matters: You stop chasing ghosts and start building momentum with the right people.

2. Deals Getting Stuck Midway (aka the Graveyard Zone)

The problem: Everything starts hot—then suddenly, radio silence. Welcome to purgatory.

The fix: Use AI to spot stalled deals before they flatline.

Tools that help:

• Clari – Forecasts risk and pipeline health using historical data and engagement trends.
• Revenue.io – Flags deals showing signs of stalling or rep fatigue.
• Tenali AI – Not only detects hesitation in real-time but suggests what to say during the call to move things forward.

Why it matters: You don’t waste three more weeks wondering if the deal is alive. You get the truth early—and act fast.

3. Reps Drowning in Admin, Not Selling

The problem: Instead of talking to customers, reps are stuck updating Salesforce, scheduling meetings, or searching for a 3-year-old PDF.

The fix: Let AI handle the grunt work.

Tools that help:

• Scratchpad – Instantly updates Salesforce without switching tabs.
• Fireflies.ai / Fathom – Create auto-generated meeting notes and transcripts.
• Tenali AI – Summarizes meetings, updates CRM, sends follow-up emails, and pulls up docs—without you lifting a finger.

Why it matters: More selling time. Less “where did I save that deck?” energy.

4. Reps Can’t Be Experts on Everything

The problem: One prospect asks about ROI, another about SSO compliance—and the rep can only confidently answer one.

The fix: Real-time assistance during calls.

Tools that help:

• Creable – Assists reps with live contextual coaching based on buyer intent.
• Tenali AI – Instantly answers complex questions (e.g. “How do you integrate with Okta?”) mid-call by pulling from internal docs, product sheets, and your company’s website.

Why it matters: You stop deferring questions to an SE. You answer with confidence, right there and then.

5. Coaching Comes Too Late

The problem: You lost the deal… then got feedback. Awesome. Very helpful. Too bad it’s over.

The fix: Coach during the deal—not just after.

Tools that help:

• TL;DR Notetaker – Automatically captures key moments, objections, action items, and summaries—without making you rewatch a 60-minute call. It highlights where things went sideways while the call is still happening.
• Wingman by Clari – Tracks whether reps are sticking to the sales methodology (like MEDDIC or SPICED), and nudges them in real-time with cue cards, objection handling scripts, and next-step reminders.
• Tenali AI – Lives inside your calls, understands context, and responds like your smartest SE—surfacing pricing comparisons, compliance docs, or competitive insights the moment you need them.

Why it matters: Reps don’t just get coached—they get saved before the deal derails.

Final Thought: AI Won’t Replace Grit—But It Will Save Your Time (and Your Deals)

You still need to build trust, tell a great story, and show up when it counts. But AI? It’s like adding another brain to your team—one that doesn’t sleep, doesn’t forget, and doesn’t mind doing the boring stuff.

Enterprise sales will always be messy. But with the right tools? It doesn’t have to be so painful.

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P.S. If you want to try what reps are calling the “SE-in-my-ear,” check out Tenali AI. It’s not just another call recorder. It’s the only AI that helps during the call, not just after.

Try it free. Or don’t. But your future self (and your forecast) might thank you.