Guides
Straight answers to the questions revenue leaders face when the number is on the line. Each guide gives the short answer, the questions to ask and a case study, from Jason Mesiarik.
New in the seat
5 guides
What should a new CRO do in the first 100 days?Learn what is true before you change much. Find out what the CEO and the board believe the number will be, and test that belief against the pipeline and your best customers. Make a few visible decisions early. Earn the right to change the bigger things. By day 100, commit to something the board can check.How do you assess a sales team you inherited?Assess an inherited team on evidence gathered over weeks. Separate what each person did from what their territory and quota plan handed them. Watch sellers work live deals, and watch managers review them. Ask customers which sellers they trust. Before any change, weigh the cost of 60 more days against the cost of getting it wrong.What should your first board update as CRO cover?Show the board what you have verified and what you still take on trust. Where your view of the number differs from the plan, say so and bring the evidence. Commit to one result the board can track between meetings, and ask for what you need. A short, true update earns more trust than a full one.What should a new CRO ask the CEO and CFO first?Ask how this year's number was set and what it assumes. Ask how it has moved against plan in past years, and why. Learn the limits on cash and hiring, and who decides on price, discounts, territories and headcount. The CFO's view of revenue quality matters as much as the CEO's growth story.What changes when you step up from sales manager to VP of Sales?You stop running deals and start running the people who run them. Your number now arrives through your managers, so your time moves to developing them. You also own a forecast you did not build deal by deal, and you work with peers across the company. Some habits that made you a strong manager will hold your managers back.
Pipeline and forecast
5 guides
How do you tell if a deal is real?A deal is real when the buyer is doing things. They agreed to a dated next step. You have access to the person who signs. They have a reason to act this quarter, and both sides can see the steps to a signature. When all the recent activity sits on the seller's side, the deal is a hope.Why do sales forecasts miss?Sales forecasts miss for a handful of human reasons. Sellers are optimistic. Close dates move while the deal stays in the forecast. Buyers walk away with no decision, and those deals stay in the forecast too long. Stage names mean different things to different reps. Fix the definitions and the inspection, and the math improves.How much pipeline coverage do you need?You need enough pipeline to close the gap at the win rate your team earns on deals that can close inside the period. Three times coverage is a rule of thumb that fits a win rate near one in three. Coverage misleads when it counts deals whose close dates have moved or deals too early to close in time.When should a CRO step into a deal?Step in when your presence changes what the buyer can decide. That might be a peer conversation with their executive or a commitment only you can make. A relationship at risk may need you too. Stay out when you would only add pressure or take over the deal. Decide with the seller and manager, and hand it back.What should a weekly pipeline review answer?A weekly pipeline review exists to make decisions. It settles which deals get help and from whom, and which leave the forecast. The team's next week follows from those choices. It should show what changed since the last review and why, including what the buyer did. When it only reads the CRM back, it has become a status meeting.
Coaching the managers
5 guides
What does good sales-manager coaching look like?Good coaching changes how a rep works, and the change shows up in the rep's next customer conversation. Reviewing the numbers is a separate job. To see which managers coach well, watch them coach and ask their reps what they now do differently. Check where each manager's time goes, and ask who coaches the managers.Is it a skill problem or a will problem?Look at evidence before motive. A skill gap shows when someone tries and the work falls short. A will gap shows when someone can do the work and does not. Check the system first, because territory, tools, pay and your own coaching often produce what looks like will. The fixes differ, so the label matters.How do you spot a manager who inspects instead of reporting?A reporting manager reads the CRM back to you. An inspecting manager tests each deal against what the buyer has done and changes the forecast when the evidence says so. You see the difference in what the manager knows beyond the CRM and the deals they move. Their forecast record and their sellers tell you the rest.How should you handle a top producer who hurts the team?Count the whole cost before you weigh the number. That cost includes the sellers who leave or stop trying and the customers who feel it. It also includes what the team learns you will tolerate. Name the behavior early, in private, against the standard everyone else meets. If it continues, act, because the team watches what you allow.Is this rep ready for promotion to manager?Promote on evidence that the person makes other sellers better, a different skill from selling. Look for someone peers already go to for help, who can also explain why deals are won or lost. Ask why they want the job. Let them try parts of the role first, and plan for the sales you lose when they stop selling.
Private equity
5 guides
What do operating partners look for in a CRO?Operating partners look for a CRO who knows the real number and says it early. Then they look for a team that delivers that number repeatably. Predictability and candor come first. Growth comes after. A miss you flag in month four costs far less trust than a surprise in month eleven. Show the reasons deal by deal.How do you merge sales teams after an add-on acquisition?Protect the acquired customers and the people they trust first. Get both teams to agree, in plain words, what a qualified opportunity means. Align pay so the behavior you want is the behavior that earns. Move the acquired team onto your systems once those definitions hold, because a new system will carry an old disagreement forward.What belongs in a commercial update to the sponsor?Tell the sponsor what changed since last month and why, with the evidence, and tie each change to the value creation plan line it touches. Share the early signals that show where the number is heading. Bring bad news in the month you first see it, and say what caused it and how you are responding.How do you build one sales standard across a buy-and-build platform?Share a small set of meanings across every company on the platform, for example when an agreement counts as renewed or a customer as lost, so the sponsor can compare companies and add up their numbers. Let each company keep its selling style and relationships, and leave most tools alone until those meanings hold. Standardize what you need to compare.What should commercial due diligence ask about a sales team?Ask whether the revenue repeats and whether this team can grow it. Learn how much comes from agreements that renew and which customers would leave with one person. Compare past forecasts with results, and check what buyers have done on the largest deals. The answers show what you are buying and what the first 100 days will cost.
Services growth
6 guides
How do you grow service agreement renewals?Renewals slip when nobody owns them before the notice date. Put a name on every service agreement renewal 90 days before that date. Open the conversation early with proof of what the agreement delivered this year, and settle any open service problem before price comes up. Renewals are pipeline with dates and belong in the pipeline review.How do you turn inspections into repair revenue?Deficiencies become repair work when one person owns each one from the technician's report to the customer's approval. That owner gets the quote to the customer while the finding is fresh and explains what an open deficiency means for the building. Quotes stall in the gap between report and sale, where nobody owns them.What is a good bid-hit rate, and how do you raise it?There is no single good number. Rates move with the trade and the type of work, and the ranges trade press repeats are one consultant's observations, published without a method. The rate rises when you bid fewer jobs you are built to win and learn why you lost the others. Track it by type of work and by customer.How do you run branch sales teams to one standard?Agree on a few shared meanings, such as what counts as a qualified opportunity or a renewal at risk, and let branches differ on the rest. Compare branches on those shared meanings and adjust for what each market holds. Give each branch manager ownership of the result, and spend your time where the gaps between branches teach you something.How do commercial services buyers plan their budgets?Most commercial buyers set next year's budget before the year begins. Service agreements and routine repairs usually sit in the operating budget. Replacements and major repairs compete for capital. Learn each customer's budget calendar and who builds the request, and give the facility manager what they need while the plan is open. Work that misses it often waits a year.How should you pay salespeople in a services company?Pay sellers for what the business needs this year, and make sure the plan does not punish the work that keeps customers. Service agreements and projects make money differently, so a plan that pays on bookings alone can reward the wrong deals. Check that margin, renewals and collected cash show up in pay. Keep it simple enough to explain.
AI for revenue teams
5 guides
Should you build it in Claude or buy it?You can build a lot with Claude or any capable model. The harder question is what it takes to keep it working. That means data connections, proof the answers stay right, security, and an owner when people and systems change. Build what is core to how you win and staffed to maintain. Buy what you need working this quarter.What can AI do for sales managers, and what can't it?AI can read more deal history and account notes than any manager has time for, then draft the summary and the prep. Judgment about people stays with the manager, and so do the coaching conversation and customer trade-offs. Know what it reads and how often it is right. Name the person who acts on it.AI agents in the revenue team: who owns the number?The CRO still owns the number. Agents change who does the work, and accountability stays with people. Put a person's name on every agent that writes to customers or changes records. Decide which of its actions wait for a person's approval, and keep a record of what each agent did so you can trace any forecast change.How do you evaluate AI tools for a revenue team?Test the tool on your own data, with the people who will use it, against questions you already know the answers to. Ask what it reads and where that data goes. Ask how you will know when its answers get worse. A demo on the vendor's data proves the vendor's data.Do you still need sales managers if AI coaches reps?Yes. AI can review more customer conversations and give more feedback than any manager, and that changes the job. The manager still owns judgment about people, the coaching that changes how a rep sells, and accountability for the team's number. Expect managers to spend fewer hours finding problems and more on the conversations that fix them.
Ask these questions of your own number.
Management OS tells the revenue leader where to act to hit the number: which deals are real, who needs coaching and how, and where your own involvement moves it.