Shaili Haridas

Gainsight released their Customer Success Index for 2025 and their CCO Brent Krempges provided some really solid insights. For anyone keeping track of the trends within the CS world, there shouldn't be any big surprises. That being said, the data to support Brent's insights is really helpful. Anyone can (and does!) say "AI is changing CS" but seeing that AI adoption on CS teams is up 8% YoY (52% in 2025), but still trailing other GTM teams by quite a bit (81% for marketing, 69% for sales) shows how much of a gap there is... and what a massive opportunity there is for CS teams and vendors in the space that support these teams. As someone who cares a lot about all of the trends impacting CS teams, especially digital adoption, I was drawn to the last slide titled "Programs Utilized in Digital CS Approach" (see image below). Onboarding is already a top digital program (42%)—but not maxed out. Nearly half of CS orgs run digital onboarding, which means buyers now expect this experience. The flip side: 58% still don’t, so there’s real whitespace to differentiate with a great digital launch flow. Digital onboarding isn’t optional anymore. If your onboarding still lives in email threads, you’re leaking TTV. Advocacy/NPS (54%) and Training/Cert (50%) outrank onboarding. Teams lean heavily on education and voice-of-customer programs. Your onboarding should interlock with both: auto-enroll new users into bite-size training and schedule the first NPS check after the “first value” milestone. Make onboarding the front door to advocacy. Feature release experience (44%) is close to onboarding. Treat onboarding as the first release customers experience—same mechanics: announcements, in-app walkthroughs, and checklists tied to value moments. Renewals (27%) and Expansion (23%) are under-digitized. Big opportunity to connect onboarding milestones to auto-renew eligibility and expansion triggers (e.g., “90% checklist completion + 3 key features adopted → prompt for seats/module upsell”). Executive engagement is almost untouched (4%). Build a lightweight, executive-only onboarding track: a one-page ROI dashboard and a monthly email summarizing time-to-value, risk, and next milestone. This is low competition and high influence. Needless to say, I am very bullish on the CS space in 2026 and am fortunate to be in a position to help CS teams improve their customer onboarding experience.

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How to go from SMB AE to MM AE (In 6 simple steps) 1. Pick a company that actually promotes. If you’re at a place that doesn’t grow fast and doesn’t promote internally, the odds are already stacked against you. You can be a top performer and still wait forever because the culture just doesn’t value internal mobility. You want to be somewhere that expects and plans to promote from within. 2. Get to the top of the leaderboard. Every interview process I’ve ever seen starts the same way. The leaderboard. That’s the eligibility filter. So that’s where 100 percent of your focus should go. Until you're at the top consistently that should be your #1 focus. 3. Be a MM AE before you’re a MM AE Find out what actually matters in MM. What’s different. What’s expected. Bigger, more complex deals. More outbound. More strategy. More multi-threading. Then go get results in those areas while you’re still in SMB. That way in the interview you can say. “Here’s how I’m already doing the mid-market job.” Nothing builds confidence like results. 4. Build real relationships with the MM team. Get close to the MM AEs. Learn what they’re working on. What their priorities are. What tools they’re using. What’s working. What isn’t. So when your interview comes around, it’s clear you already understand the role. You’re not walking into a whole new world. You’ve already been around the team and the expectations. 5. Build your internal brand with the hiring team. This is one of the most underrated moves. Find out the #1 priority for MM. Let’s say it’s outbound. Go get results. And then send a no ask message to the hiring manager: “Hey, I heard outbound was the focus this quarter. Booked 7 meetings this month using my cold call flow. Documented it in a playbook. Thought I’d share in case it’s useful.” That's one of the most gangster things you can do. 6. Prep early. Prep often. Don’t wait for the interview process to start preparing. Start building now. A highlight deck. A deal room. Case studies. References. Anything that strengthens your narrative. So when the interview actually opens up. You already have everything done. You just tweak it. Meanwhile everyone else is scrambling. 7. Have a competitive mindset. This is the part most people avoid saying out loud. But it’s the truth. You’re competing. You need to ask yourself constantly. “If someone else has similar numbers, how do I make the case that I’m better?” - That could be your prep. - Your brand. - Your relationships. - Your execution. What you don’t want to do is assume that great work alone gets you promoted. It can. But it’s not the optimal strategy. The optimal strategy is to think competitively. Strategically. And position yourself to win. What did I miss? - Mike G 👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

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Most revenue problems aren’t strategy problems. They’re judgment problems. I’ve seen organizations with strong products, capable sellers, and plenty of pipeline still miss badly. Not because they lacked effort or tooling, but because they struggled to separate signal from noise. When judgment is weak, teams over-index on activity, dashboards, and optimism. When judgment is strong, leaders know which numbers matter, which conversations matter, and which decisions can’t wait. Process doesn’t fix judgment. Tools don’t fix judgment. But good judgment makes both far more effective.

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Biggest hack for building early stage GTM selling into SMB... hire SDRs. transition them into AE roles quick... No need to hire AEs externally. just nail the process of sourcing, hiring, training, onboarding SDR only. External AE hires add over $200k of risk in year 1. If you run a simple sales process, make your life a hell of a lot easier and just nail hiring & onboarding for 1 role. Let the cream rise to the top, promote them fast. They'll ramp immediately and source their own deals. You can run this play for a longgggg time. I'm running a test to do this for you... if you're doing this, shoot me a note.

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Good luck solo selling in 2026. Team selling is no longer a strategy, it’s a GTM essential. If you’re going to spend months in a cycle, you’re going to need a lot of teammates playing a lot of different roles. Especially if it’s technical and 6 figures plus in value. Every team will look different, but the personas you’ll likely need to play a part: SDR Demand Gen Marketing Core Account Executive Product Specialist/SME Solutions Engineer Alliances Channel Competitive intel Product/Engineering Leader Sales and Solutions Engineering Leader Legal Customer Success Professional Services Executive Sponsor And I’m probably missing some. I used to think this type of selling was a sign of my weakness as a seller. “I should be able to handle this cycle myself.” Then I started selling in the higher segments into the Fortune 500. I quickly realized that prospecting and multi-threading was better as a team. As was prepping, tackling meetings, aligning to move deals forward. Really all of it. Does it make the “cost of sale” go up? Maybe, but I’d also argue that when done right it makes the deal size and win rate go up as well. #karpediem

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What if we’re celebrating the wrong sales leadership metrics? 🤔 ARR. ACV. TCV. Pipeline. Important, sure…but they don’t tell me if you’re a great leader. Here are the metrics that actually do 👇 (And funny enough… they never show up on a dashboard.) The 4 most underrated sales leadership metrics: 1️⃣ How many former reps would choose to work for you again? People don’t voluntarily sign up for chaos. If they’d run it back, you did something right. 2️⃣ How many reps have you promoted? Extra credit if you promoted someone out of your org or into leadership. That’s development, execution and advocacy coming together. 3️⃣ How many reps have earned multiple promotions after your team? That’s coaching that sticks, skills that travel, not just tactics for one market. 4️⃣ How many reps left for something better (by choice)? Low voluntary attrition + upward career trajectory = clarity, trust, and real growth. Let’s normalize these metrics. Because they tell you everything you need to know about a leader.

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Love the message here! I’ve had the privilege to work with some truly world class teams in my career, and most, if not all, had this same problem. My favourite line here and one that cannot be be overstated enough : “Because when your best CSM leaves, they don't just take their title. They take the relationships that keep your biggest accounts from picking up a competitor's call.”

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Most CSMs still prep for customer kickoffs like it’s 2020: • Watch 1–2 hours of sales calls in Gong, Chorus, Clari, Zoom • Skim random notes • Pray nothing “special” was promised It feels responsible. But it destroys your capacity. You are paid to move accounts, NOT to rewatch meetings. Here’s what top CSMs are doing instead in 2026: - Let AI pull every promise, timeline, and risk from the call - Run a focused 15-min handoff with Sales to confirm facts - Use a one-pager so every onboarding starts with the same clarity - Track a simple ROI story that your VP actually cares about In this week’s edition of The Customer Success Café, I walk through: - The 5-min AI kickoff prep workflow - The exact prompts I use in Gong/Chorus/Clari - A 15-min handoff script you can steal - The “show me the snippet” rule for special terms - A one-pager template and KPI mini-pack for your VP This isn’t theory. It’s the exact system that cuts kickoff prep by 80–90% while reducing “but Sales said…” drama. If you want this kind of breakdown in your inbox every week, join 4,300+ CS pros, revenue leaders, and operators who already read The CS Café: 👉 Subscribe now for free to get weekly systems, not fluff. #CustomerSuccess #CSM #NRR #SaaS #Gong #Chorus #Zoom #RevenueLeadership

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