90-Day Milestone Planning for Sales Change

CEO: I'm firing our VP Sales. ME: How long have they been there? CEO: Almost 90 days. No major sales impact - it’s driving me crazy. ME: How long is your average sales cycle? CEO: Around 100 days. But they had a big pipeline... ME: Got it. And your SDRs and Marketing? CEO: We have one junior marketer running our blog/social. Occasional inbound demos, but our VP Sales hired first outbound SDRs. Also replaced 3 of 5 AEs. ME: Can I be direct with you? CEO: I can take it. ME: So your VP inherited a struggling team, replaced most AEs (so pipeline's probably weak), built outbound from scratch, had no marketing support—and you expected revenue impact faster than your sales cycle? CEO: Well, when you put it like that… —— I wish this was rare. It isn’t. Why? Because we keep expecting VPs to be magicians. To instantly ‘save the day’. Then blame them for results they had no time or tools to achieve. Realistically, here's what your VP can do in 90 days: 1. Assess and restructure your sales team 2. Hire stronger talent (3 AEs & SDRs is a lot) 3. Align sales targets realistically (to #1) 4. Deeply learn your market & product 5. Co-sell -> grab quick wins (if the pipeline is real!) 6. Coach team -> improve deal velocity (next Qtr) 7. Build internal alliances -> improve collaboration 8. Build better tools & processes -> save time, reduce friction But the board expects immediate revenue?... That's exactly the issue: Expectations. YOU hired them. Set realistic expectations. Protect your leaders. Firing too soon destroys confidence, morale, and leaves chaos behind. Thinking of firing after 90 days? Stop. Reflect. Yes, great VPs must create immediate IMPACT. But immediate REVENUE depends entirely on what they inherit: Outbound from scratch? Takes ~6mo. No marketing? Even slower. Replacing half your team? Expect delays. Weak pipeline? No quick wins. Revenue requires foundations. VPs aren't miracle workers. Give them a foundation—or the time to build it.

Your first 90 days with a customer can make or break the entire relationship. I've seen it happen too many times: - Great sales process - Solid product demo - Strong contract value - Excited stakeholders Then onboarding happens. And everything falls apart. Why? Most companies treat onboarding like a checklist: - Setup call ✓ - Product training ✓ - Technical integration ✓ - Documentation shared ✓ But here's the truth about onboarding: It's not about your process. It's about their success. After managing hundreds of onboarding sessions, here's what I've learned: The best onboarding isn't standard. It's personalized. Think about it: - Every customer has different goals - Every team has different challenges - Every organization has different paces - Every stakeholder has different priorities Your onboarding needs to reflect this. Here's what works: 1. Start with clear expectations - Define success metrics upfront - Set realistic timelines - Map out key milestones - Align on responsibilities 2. Build a dedicated team - Assign specialists who understand their industry - Create cross-functional support - Have clear escalation paths - Enable quick problem-solving 3. Monitor health signals - Track early usage patterns - Watch engagement levels - Note stakeholder participation - Measure progress velocity 4. Automate the right things - Regular check-in reminders - Progress updates - Resource sharing - Usage alerts But here's where most companies fail: They don't plan for challenges: - Low customer engagement - Complex technical integrations - Unclear success metrics - Resource constraints - Scalability issues The solution? Build feedback loops: - Collect input at every stage - Adjust plans based on signals - Iterate on materials - Improve processes continuously Remember: Onboarding isn't about getting customers to use your product. It's about helping them achieve their goals through your product. The first 90 days set the tone for everything that follows. Make them count. What's your approach to customer onboarding? What challenges have you faced? ------------------ ▶️ Want to see more content like this and also connect with other CS & SaaS enthusiasts? You should join Tidbits. We do short round-ups a few times a week to help you learn what it takes to be a top-notch customer success professional. Join 1993+ community members! 💥 [link in the comments section]

2026 is where we are seeing the end of the Quarterly Business Review (QBRs). And something new is taking over. The Review was always a little complex. No executive wants to join a meeting to look at a 40-slide autopsy of the last three months. They don't want a history lesson; they want a roadmap. What's taking over is the Forward-Looking Strategy (FLS). The shift is moving from being a tool reporter to a business architect. It's about stopping the "here is what you did" and starting the "here is where we are taking you." To make this transition real, we need to coach our teams to change the practical anatomy of these meetings: 1) The 10/90 Rule Use past data for one reason only: validate ROI. Spend 10% there. Then spend 90% on the next 12 weeks. If a CSM is still walking through adoption charts for 40 minutes, they've already lost the room. 2) Gap Analysis over Feature Updates Executives don't buy features. They buy progress. Show the gap between where the customer is and where they said they need to be by year-end. Then pick the 2–3 workflows that will close that gap by next quarter. Clean. Specific. Measurable. 3) Executive Resource Mapping Retire: "Anything else you need from us?" Replace it with: "To hit this 90-day outcome, we need two hours from your DevOps lead in March. Can we lock that in now?" Strategy without resourcing is performance art. 4) A Mutual Action Plan (MAP) that behaves like a project plan Never leave without a shared doc with names, dates, and ownership on both sides. A MAP is not a polite checklist. It's the operating system for the next 90 days that allows for collaboration and execution. And here's the real purpose of this transition: It's CS stepping into the role it was always meant to play. A strong CSM is not a meeting host. They're a strategic thinker who understands the customer's business well enough to see what's coming next, name the risk early, and guide the next set of moves with confidence. Forward-looking strategy is how CSMs become the owners of outcomes, not the keepers of updates. When a customer walks away thinking, "They understand our world and they're helping us win," CS has done its job. That's the change taking over in 2026. And it's a good one.

It's a new year and you are the new VP of sales. Your predecessor didn't make it. You are stepping into a new enterprise organization. The clock is ticking, expectations are high, there are 100 problems to fix, where do you start? Here's the exact framework I would use to diagnose my sales organization and GTM readiness in my first 90 days (and hopefully avoid becoming another casualty) Days 1-30: Team & Pipeline Deep Dive This is about understanding your current reality. Don't make any big moves yet. • Conduct 1:1s with every rep, focusing on their deal inspection process and client relationships. I Listen more than I talk. I'm looking for patterns in how they sell, not just what they sell. • Run a full pipeline audit - not just the numbers, but the stories behind them. When I hear "this is about to close" I will understand how good the team is re/forecast accuracy. • Review the last 6 months of win/loss data. The deals they lost tell a more important story than the ones they won. Red flags to watch for: - Reps who can't articulate their customers' business problems - Massive end-of-quarter deal pushes - Over-reliance on discounting to close Days 31-60: Systems & Process Analysis Now I'm looking at HOW the work gets done. I'll usually find thousands of problems worth addressing here. But before I make changes, I'll focus on: • Shadow discovery calls across team. I'm not looking to hear a perfect pitch delivery - I'm assessing if they're asking the right questions. • Audit tech stack usage. Low adoption usually means broken processes, not bad tools. • Review account plans for top 10 customers. The depth of these plans reveals your team's strategic thinking. Warning signs: - Inconsistent sales methodologies across teams - Customer success teams being surprised by "closed" deals - Missing or outdated documentation in your CRM Days 61-90: Strategic Realignment Time to connect the dots and plan your path forward. Key activities: • Map your ideal customer profile against your actual closed deals. The gap between these tells you where your positioning is breaking down. • Assess your competitive intelligence process. Your team should know why they win AND lose against each competitor. If they don't, you have a big problem. (We'll talk about Training Thursday's at a future post) • Review territory design and quota capacity planning. Misalignment here is often the root cause of missed numbers. (In case the above is working) Many incoming new sales leaders fail because they try to fix everything at once. The framework above keeps you focused on understanding before acting. What other areas would you evaluate in your first 90 days? Let me know in the comments 👇

If I joined a new sales team tomorrow, here’s my exact 90-day plan I’d follow to ramp fast and close early. Days 1–30: I start with my 3 P’s - I need to have these in place first. People – Meet my internal teams and ask how I can support them? Product – Master the value prop, positioning, and competition. Prospect – Research the territory and revisit old CRM opps. Track what I’m learning & where I need clarity. Helpful for other new hires. Save key talk tracks, key slides, discovery questions, etc. Days 31–60: Build Pipeline. What patterns am I seeing across calls? Good insights for marketing/product. Build my territory plan by size, industry, and persona. Use Sales Navigator to build smart, segmented lists. Write custom messaging tied to use cases. Reconnect with “old opp” buyers. Visit in person. Days 61–90: Evaluate, Refine, Accelerate. Record my process, offer to mentor a newer rep, capture best practices. Audit my pipeline, What’s real vs. noise? Review discovery-to-opp conversion. Identify product/process gaps. Team with partners. Prioritize revenue-generating activities only. Some companies I’ve worked for have a plan and some don’t. Whether they do or not, starting a new role can be overwhelming but I believe starting with the people is the ultimate key to success. Once you understand the people, then the product, it's much easier to have client conversations. Let me know if you have any questions - go get em!

You got the meeting. Congratulations. Now the real work begins. The high from a great first meeting is a familiar feeling. The conversation flowed, you connected on shared interests, and the potential for a significant gift felt within reach. But a week later, that energy often dissipates into uncertainty. That's because the most successful fundraisers know the first meeting isn't the finish line. It's the starting gun. The 90 days after that meeting are what separate a transformative gift from a dead end. It’s not about just "checking in." It's about a disciplined, value-driven cultivation plan. The 24-Hour Rule: Your follow-up email should be sent within 24 hours. It should thank them, briefly summarize what you heard, and confirm the next steps. This isn't just polite; it's professional. Go Beyond another "Meeting": Instead of asking for a second meeting, offer a custom engagement. An introduction to a board member with a shared background. A behind-the-scenes tour of a program they showed interest in. The 90-Day Cadence: Map out a series of high-value touchpoints. Think personalized impact reports, invitations to exclusive (small) events, or even a handwritten note referencing a topic from your conversation. One Head of Development I worked with secured a meeting with a retired tech executive. Her 24-hour follow-up was perfect. But she didn't stop there. Over the next two months, she introduced him via email to a program director who shared his passion for data, sent him a short, personalized video from a student in that program, and mailed him a copy of a book on philanthropy she had mentioned. She never asked for another meeting. He called her to proactively schedule one, and their conversation shifted from "if" he would give to "how" he would give. The first meeting gets their attention. The follow-up earns their trust. What's your most effective follow-up strategy after a great first meeting?

"Marcus, help. My VP just asked for my 90-day operating plan and I have no idea what that means." This call came in yesterday from a panicked AE. Most reps would have thrown together some activity metrics and hoped for the best. Instead, here's exactly what we built together: WEEK 1-2: Account Intelligence Phase → Deep dive analysis of top 10 target accounts → Identify all decision makers and influencers → Map current business priorities and initiatives → Research compelling events driving urgency WEEK 3-8: Discovery and Champion Building Phase → Run structured discovery calls with qualified prospects → Build champions in each target account → Quantify specific business impact and costs → Create urgency around solving identified problems WEEK 9-12: Demo and Advancement Phase → Deliver customized demos to qualified opportunities → Multi-thread with all decision makers → Present compelling business case → Advance opportunities to final decision stage The result? He presented this plan to his VP, executed flawlessly, and got promoted 3 months later. Here's the key insight most reps miss: Your leadership doesn't care about your activities. They care about your outcomes. They don't want to hear "I'll make 100 calls per day." They want to hear "I'll generate $2M in qualified pipeline by identifying compelling events in our top target accounts and building champions who can advocate for our solution." Stop thinking like a rep. Start thinking like a business owner. Your 90-day plan should read like a strategic business initiative, not a task list. — Want to see a LIVE coaching call of mine? Go here: https://lnkd.in/gbr8DKb8

"We need these reports ASAP". If you've heard this before, you know those reports are only as good as the data they're built on. And in most situations, that data sucks. Your HubSpot instance probably has the following: • Inconsistent lifecycle stages • Unclear deal definitions • Mixed-up customer status • Properties nobody uses • Reports nobody trusts The root cause? Building without blueprints. Before touching HubSpot, we align on four core documents: 1. 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗝𝗼𝘂𝗿𝗻𝗲𝘆 𝗠𝗮𝗽 Defines exactly how leads move through: • Marketing stages • MQL/SQL criteria • Sales handoffs • Post-sale markers • Revenue taxonomy 2. 𝗦𝗮𝗹𝗲𝘀 𝗠𝗮𝗽 Maps your unique: • Deal stages • Exit criteria • Required fields • Probability markers • Closed/lost reasons 3. 𝗣𝗼𝘀𝘁-𝘀𝗮𝗹𝗲 𝗠𝗮𝗽 Standardizes: • Onboarding stages and pipelines • Health scores (via HubSpot) • Expansion signals • Churn indicators 4.  𝗗𝗮𝘁𝗮 𝗗𝗶𝗰𝘁𝗶𝗼𝗻𝗮𝗿𝘆 & 𝗖𝗥𝗠 𝘁𝗮𝘅𝗼𝗻𝗼𝗺𝘆 Aligns teams on: • Property & Field definitions • Required properties • Reporting standards • Naming conventions inside your CRM    Then We Build: The 90-Day Implementation – with definitions clear, we implement in phases: 𝗥𝗲𝘃𝗲𝗻𝘂𝗲 𝗙𝗼𝘂𝗻𝗱𝗮𝘁𝗶𝗼𝗻 (𝗗𝗮𝘆𝘀 𝟭-𝟭𝟱) • Configure lifecycle stages and automation (includes lead object) • Create custom properties (UTMs + hidden fields) • Basic Account/Lead scoring (with new Beta) • Core integrations 𝗦𝗮𝗹𝗲𝘀 𝗜𝗻𝘁𝗲𝗹𝗹𝗶𝗴𝗲𝗻𝗰𝗲 (𝗗𝗮𝘆𝘀 𝟭𝟱-𝟯𝟬) • Configure deal stages (and the lead object) • Forecasting and goals • Routing and lead assignments (territory) • Individual and team dashboards (v1) 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗛𝗲𝗮𝗹𝘁𝗵 (𝗗𝗮𝘆𝘀 𝟯𝟬-𝟰𝟱) • Set up ticket pipelines. • Build customer health score. • Automation of renewals • Clear definition of upsell/renewal triggers 𝗗𝗮𝘁𝗮 𝗤𝘂𝗮𝗹𝗶𝘁𝘆 (𝗗𝗮𝘆𝘀 𝟰𝟱-𝟲𝟬) Using Data Dictionary & Taxonomy : • Setup data hygiene dashboards • Deduplication via Koalify • Standardized naming and folder structure • Error reporting and notifications    𝗘𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 (𝗗𝗮𝘆𝘀 𝟲𝟬-𝟵𝟬) Tell the story clearly through: • 𝗧𝗶𝗺𝗲 𝗠𝗲𝘁𝗿𝗶𝗰𝘀: Track time at each stage to find and remove roadblocks, improving the overall customer experience. • 𝗖𝗼𝗻𝘃𝗲𝗿𝘀𝗶𝗼𝗻 𝗠𝗲𝘁𝗿𝗶𝗰𝘀: Identify drop-off points across the journey to refine engagement strategies. • 𝗩𝗼𝗹𝘂𝗺𝗲 𝗠𝗲𝘁𝗿𝗶𝗰𝘀: Monitor volume at each stage to ensure a steady flow from lead to loyal customer.    There is a better way to get where you're going, but it takes the right foundation. #hubspot #crm #data