Sales Assembly

If your CEO asks for deal updates in Slack, don’t expect reps to update Salesforce. You can throw all the tech, training, and sales ops resources you want at CRM adoption - but if leadership isn’t leading by example, none of it will stick. Here's the tl;dr: Reps don’t hate updating Salesforce because they’re lazy. They hate it because they know no one actually uses it. When leaders bypass the CRM - asking for updates in Slack, emails, or meetings - they send a clear message: “This system doesn’t matter. Your notes don’t matter. Just tell me directly.” And that’s how $100k+ Salesforce investments turn into glorified Rolodexes. So, how do you fix it? 1. Top-down adoption Start with the CEO. If they want deal updates, they need to ask for them in Salesforce. Chatter, Slack integrations, whatever it takes...but it has to flow through the system. 2. Make sales managers accountable Reps won’t change unless their managers enforce it. Run pipeline reviews directly from Salesforce dashboards. No exceptions. If it’s not in Salesforce, it doesn’t exist. 3. Quantify the pain Show reps how missing data costs them deals. Lost follow ups, misaligned hand offs, deals slipping through the cracks...all because the CRM isn’t up to date. 4. Reward the right behaviors Sales culture loves to celebrate closers. But what about the reps who close and keep a clean pipeline? Make data hygiene part of what gets recognized (and compensated). The reality is that CRM adoption isn’t a sales ops problem - it’s a leadership problem. If the top isn’t setting the example, the bottom won’t follow. And until that changes, you’ll keep throwing money at Salesforce while your reps keep their real pipeline in a Google Doc.

I’m happy to share that I’ve obtained a new certification: Product Adoption Certification from Sales Assembly!

A group meeting without 1:1 follow ups is like a wedding without a photographer. Sure, it happened. But if no one remembers it, what did it actually do? Reps spend hours prepping for the big meeting. Deck’s tight. Stakeholders are there. Some smiles, some nods, maybe even a few good questions. Then they send…a generic recap to the thread. And then they wonder why momentum stalls. Here’s how to turn polite applause into pipeline movement: 1. 1:1 messages are your post game locker room. Want buy in? Don’t rely on the group chat. Send tailored notes to each stakeholder. “You flagged onboarding risk...here’s how we handled that for [peer company].” It shows you listened - and it invites the next conversation. 2. Executive stakeholders don’t care about your product. They care about their scoreboard. Skip the features. Speak to what moves their metrics. “Here’s how this helps you reduce implementation time by 30%” hits harder than a 20-slide deck. 3. Surface the quiet no. Group meetings are a performance. Objections get buried. But a single DM like “Curious to get your honest take...any hesitation on your side?” can unlock the real blockers. I know of a rep who's entire deal turned when a silent stakeholder said, “Honestly, I didn’t get it.” That message led to a 15 minute call. And the win. The meeting gets the attention. The follow up gets the deal. Don’t let your pitch die in the group thread.

If you’re trying to rip out an incumbent, you’re not selling your product. You’re selling a divorce. And divorces are painful. That’s why so many deals stall when prospects get cold feet. Even if their current solution is outdated, overpriced, or inefficient, switching comes with risk...real or perceived. The best reps don’t just pitch a better alternative. They make staying put feel more dangerous than making a change. Here’s how: 1. Quantify the hidden costs. Most legacy vendors survive because their costs feel lower. You need to make the real cost of staying crystal clear - lost efficiency, poor integration, security risks, opportunity costs. 2. Sell leadership on future-proofing. Execs don’t care about your feature set. They care about whether their business is positioned for the next 5-10 years. Show them how their current vendor is holding them back. 3. Make switching painless. If your migration plan isn’t airtight, you’re done. No one wants to risk an operational nightmare. The best reps have a transition playbook that makes moving feel seamless. 4. Find the internal frustrations. The people actually using the legacy system hate it. You need them championing the switch from the inside. Make their job easier, and they’ll help drive the decision. tl;dr is that people don’t leave bad vendors. They leave bad situations. Make them feel the pain of staying put, and moving will be the only logical choice.

Reminder for this week: Buyers don’t stick to deadlines unless THEY feel the consequences of missing them. Instead of anchoring to your EOM goal, tie urgency to their reality: - What happens if this isn’t solved in Q1? - How will delays affect their team’s KPIs? - Who internally is expecting this problem to be fixed...and will they ask why it isn’t? And always, always ask: “What roadblocks could slow this down?” Know them before they become last-minute deal-killers. Want to speed up your deals? Start making their deadlines more painful to miss than yours.

Hiring a CRO is like handing someone the keys to your revenue engine. But if your compensation plan’s misaligned? That engine stalls fast. Issue across the market: Too many companies compensate CROs based on what they value, not what the CRO can actually control. In a recent convo with a few of these types of folks, I heard the same debate I’ve seen on repeat: - ARR-based comp? Drives aggressive top-line growth but can overlook profitability. - EBITDA-based? Great for investor optics, but it handcuffs CROs who don’t own cost levers. - Equity-heavy packages? Long-term alignment, but risky if the vesting cliff is a mile away. Here’s my two pennies on how to get it right: - Tie 60-70% of variable comp to controllable outcomes. Focus on the team’s ARR and net retention rates. Give the CRO levers they can actually pull. - Layer in accelerators for cross-functional wins. Did they reduce churn by 10%? Unlock a kicker. Boosted average deal size by 20%? Another kicker. - Add strategic unlocks. Hitting company-wide EBITDA targets? Time to cash in a meaningful bonus. - Equity? Yes, but structure it around clear milestones...not just time-based vesting. A great CRO won’t chase just ARR or EBITDA. They’ll chase alignment - their success tied directly to the company’s success. Set them up to win, and they’ll take your revenue and your valuation with them.

Sales is like dating. You don’t propose on the first date. You pay attention, build trust, and prove you’re worth a second conversation. I was once pitched by a vendor. Early in the conversation, I mentioned that my wife, pet human, and I love to travel. I also told him two important things: 1) We wouldn’t be buying for at least two quarters. 2) We were evaluating multiple vendors and in no rush to decide. Most reps would have put me on a quarterly check-in list and moved on. This guy? He listened. - Email #1 (Same Day): A quick thank-you note...plus a restaurant recommendation in the city we were visiting. - Email #2 (One Month Later): No pitch. Just another restaurant suggestion. - Email #3 (Four Months Later): Subject line: “How was the trip??” Body: empty. I bought from him that month. After I replied, of course. Why did it work? Because he played the long game. Some reps treat sales like a sprint: push hard, push fast, get the deal. But high-value deals aren’t won in a single call. They’re won through trust, patience, and timing. Yes, you need a strong use case. Yes, ROI matters. That’s table stakes. But in a competitive deal, when everything else is equal, the buyer goes with who they trust - the rep who actually listens, remembers, and proves they’re in it for more than just the close. A desperate salesperson is like a guy proposing on the first date...it reeks of commission breath and sends buyers running. Sales isn’t about pressure - it’s about presence. Play it right, and when they’re ready to buy, you’ll be the only option that makes sense.

ABC is impossible without ABL...Always Be Learning (Sales friends, IYKYK ?? ) Enjoying the Sales Assembly lab for Revenue Managers with Todd Caponi and the peer group sessions. The value extends beyond content to collaborative discussions with peers in similar tech sales leadership roles. Creating a safe space for sharing challenges, exchanging ideas, and recognizing wins (and losses) is integral to personal growth and fostering a supportive community. Sales Assembly lab classmates, let's connect!

Selling to ENT without changing your pricing model is like showing up to a black-tie event in flip flops. MM pricing models don’t survive in enterprise sales. Why? Because selling 1,000 licenses to an enterprise isn’t 20x harder than selling 50 - but if you don’t adjust your pricing strategy, it will be 20x more painful. Enterprise buyers don’t think in per user terms. They think in budgets, forecasts, and cost centers. They want predictability, not a CPQ nightmare where they’re adjusting seat counts every quarter. If you’re moving upmarket, here’s how to avoid looking like a tourist at the grown-ups’ table: 1. Kill per-user pricing for large accounts. Enterprise CFOs see per-user models as a ticking time bomb...every new hire adds cost. Instead, sell in committed tiers, annual volume contracts, or all-you-can-eat licenses. - Instead of “$50 per user, per month,” structure it as, “$X for up to 1,000 users.” - Price for usage, not headcount - think storage, API calls, transactions, etc. 2. Enterprise doesn’t “expand naturally.” Build in expansion from day one. For MM, you can land small and grow. Enterprise doesn’t work that way. - Ramp pricing: Year 1 at 60%, Year 2 at 80%, Year 3 at 100%. Predictable growth, no CFO freak-outs. - Auto-expansion clauses: If usage exceeds X%, licenses auto-scale. Protects you from procurement pulling a “we’ll just add seats later” stunt. 3. Enterprise buyers expect to “win.” Give them a win - without losing. These buyers are trained to negotiate. They want a lower per-unit cost, but they’ll commit bigger dollars to get it. - Introduce an ENT Rate...lower per-unit cost, but higher minimum commit. CFOs love “efficiency,” and you get more ARR locked in. - Structure custom packaging that makes them feel special. Limited access to beta features, priority support, or bundled services. Want to win in enterprise? Stop selling like an SMB rep. Price for scale, control the expansion, and let procurement “win” on terms that make your CFO smile.

?? I’m excited to share that I’ve earned my Sales Assembly Certification in Risk Mitigation! ?? A big thank you to Sales Assembly for the valuable insights and training! Looking forward to applying these skills. #ProfessionalGrwoth #SalesAssebly #ContinuousLearning Impact Networking, LLC