Crafting a Strategic Forecasting Roadmap

If every rep forecasts differently, you don’t have a forecast. You have a guessing game. I’ve seen this too many times: - Some reps pick a number out of thin air and reverse-engineer the deals to match. - Others commit specific deals, but with no clear criteria for why. - Some just lowball their number so they can overdeliver. The result? A forecast that’s less science, more storytelling. When reps set their own rules, you get: - Erratic projections, making it impossible to resource properly. - Lost accountability, because reps can move the goalposts without consequence. - Misalignment with GTM teams, because RevOps, finance, and CS are forced to react to unreliable inputs. Here’s a solution: 1. Define a standard forecasting model Forecasting needs rules. Either reps commit deals based on clear criteria, or they forecast a number with justification. Mixing both = inconsistent rollups. 2. Enforce criteria for Commit deals A deal isn’t commit-worthy unless it checks key boxes: - Multithreaded (or it’s a coin flip at best) - Economic buyer engaged (champions don’t cut checks) - Procurement validated (or it’s stuck in limbo) No criteria, no commit. 3. Use data to call bullshit Reps’ confidence isn’t a data point. If their forecast is wildly different from historical conversion rates and deal stage velocity, they need coaching, not a calculator. 4. Drive home that you’re forecasting is for business planning, not just quota pressure The CFO isn’t asking for fun. If your forecast is off by 30%, you’re not just missing a number - you’re messing up hiring plans, resource allocation, and revenue projections. 5. Make reps own their forecasts Accuracy should be a coaching metric, not just a reporting function. If a rep is always 30% off, fix their deal inspection process, not just their Excel skills. A forecast isn’t a wish list…it’s a commitment. The tighter the system, the better the number. A sloppy forecasting process signals a sloppy sales org. Your forecast is either an operational asset - or a liability. That’s a choice.

If I were a Treasury leader at a high-growth company today, here are a 6 practical tenets of Cash Flow Forecasting that I’d deploy to ensure confidence and accuracy: 1) HISTORICAL DATA - start by gathering historical cash flow data from multiple sources – revenue, expenses, payroll, and other outflows. - then use this data to build a baseline forecast by identifying patterns like seasonality, subscription renewals, and recurring expenses. - it’s important to also contextualize the data by meeting with the teams involved in these functions. - too often I see early Treasurers fail to connect the dots due to a lack of understanding of the data story. 2) SYSTEMS AND DATA - connect the ERP, CRM, billing systems, and bank feeds to centralize data collection. - disaggregated data sourcing increases delays and errors, - which is why I suggest using an automation tool (like Nilus) and AI-powered forecasting to help predict future cash flows based on predictive analytics, bottom-up ERP data, and customer & vendor payment behavior. 3) SCENARIO PLANNING - build various cash flow scenarios to prepare for different outcomes - best-case, worst-case, sensitivity scenarios based on market volatility, Cx churn expectation and unforeseen costs. - by understanding a litany of scenarios that could drive the business, you will not only have a more granular understanding of business impact, but become able to more quickly connect the dots. 4) REAL-TIME ADJUSTMENTS - prioritize using tools that provide real-time visibility into cash positions across bank accounts and currencies, and set up automated alerts for significant changes (e.g., if cash balances drop below a certain threshold) so strategies can be adjusted swiftly. 5) REVIEW AND COLLAB - ensure that treasury and finance teams meet regularly to review the forecast. - forecasting shouldn’t exist in a silo—it needs to align with broader business strategies like expansion plans, investments, etc. and treasury has got to stay in the loop. 6) LIQUIDITY - manage working capital by adjusting payment schedules, accelerating collections, and optimizing idle cash for short-term investments. - liquidity is about getting cash to work efficiently, so make sure every dollar is positioned to drive value. By following these steps, your team should have greater confidence in cash forecasts, helping the CFO and great C-suite make better decisions to support growth. PS - What tips would you add?

Because with a bad forecast everything else will fail... This infographic contains 7 steps to create and improve a forecast: ✅ Step 1 - Start with Historical Data Collection & Cleaning 👉 gather and clean past sales data (ideally 3 years) 👉 remove outliers, fill in gaps, and ensure data accuracy before analysis ✅ Step 2 - Segment Your Demand 👉 break down your demand into segments to create more granular forecasts 👉 examples: volume, value, product categories, customer types, regions ✅ Step 3 - Generate a Baseline Statistical Forecast 👉 as starting point, generate a baseline forecast using statistical methods like time series analysis ✅ Step 4 - Apply Seasonality and Trend Adjustments 👉 use historical seasonal patterns and emerging trends to fine-tune your forecast for upcoming periods ✅ Step 5 - Collaborate & Fine-tune in S&OP Meetings 👉 collaborate with sales, marketing, finance, and operations to align on one consensus forecast ✅ Step 6 - Adjust for Market Intelligence 👉 incorporate insights from sales teams, marketing campaigns, external research, and product launches to adjust your baseline forecast ✅ Step 7 - Incorporate Forecasts into S&OE (Sales & Operations Execution) 👉 drive actionability in the short term based on this aligned forecast, helping the team respond quickly to deviations 💥 Bonus Step: Build a Continuous Feedback Loop 👉 track forecast accuracy by comparing actual sales to forecasted figures, and regularly update your model based on this feedback Any other steps to consider? #supplychain #salesandoperationsplanning #integratedbusinessplanning #procurement

I've been quiet 🤫 ... and quietly coming to terms with the brutal facts in front of me... I'm never going to build a LinkedIn empire. Sigh. But I do like to write, and it's been a bit. Lemonade Stand finally hit its stride and is humming along, which has meant less capacity for creating out in the open. To get back in the groove I'm doing a few quick hitters on what I've been working on with fractional clients, with some actionable tips. Roadmap "spikes" have been popular lately, especially with early stage startups (I think it's the new year vibes). Here's what it looks like: Pre-work: I provide a set of questions for the founding team to consider independently, with answers sent to me directly. We use these both as inputs for the roadmap, and to do a quick assessment on how aligned the team is on the plan for the business over the next 6-12 months. Workshop: we pick a full day we can dedicate to crafting the roadmap. Note that this is not just a product roadmap - product is the keystone, but it covers other major levers like hiring, partnerships, etc. I moderate the session to make sure we explore all our options, but also stay focused and get what we need out of the day. Tailored Roadmap: after the workshop, I craft the roadmap (based on the team's collective input) using a template that I've applied at a number of companies where I've been CPO. Basic structure is: * # 1 goal (eg "North Star") for the business - could be revenue of $X by Y date; could be profitability; could be ready to raise a Series A (and specifying what that looks like); could be a critical product milestone; etc. * Top three challenges that need to be solved to achieve that goal - we'll call these strategic themes. * Defining "what winning looks like" for each theme - how will we know if we've achieved that goal? * Initiatives - what are the investments (product, people, etc) we can make that are most likely to achieve that? * Sequencing - detailed and committed plan for the current quarter; penciled in plan for the next quarter; loose ideas for the last two quarters It ain't rocket science, but you'd be surprised how many startups resist having a plan, because it feels like it impedes nimbleness and flexibility. Anything but - it creates focus, and a disciplined way to hold one's self to account for changing your mind. Is the new idea really worth disrupting the plan? You never know unless you actually have a plan in the first place. The real magic is the implementation guidance, or how to put the plan into action: I join the team every two weeks for an hour, for the first quarter the plan is in action, to provide coaching on how to make it real, with urgency. Things we might cover there: * Prioritization - new and exciting things will pop up. Should we respond? * How to write good product stories and reqs for engineers * Simple systems for managing product work (I really like Linear) Holler if you need help, or go ahead and run a spike yourself!