This week, my guest is JD Miller, an author and SaaS sales vet with over two decades of experience in revenue leadership across private equity (PE) backed companies. I've only worked in venture backed businesses during my time in tech so it was fascinating to dig in with someone who has spent almost his whole career in the PE backed world. There was actually a lot more in common with our approaches than different and you can hear lots more about his playbooks in his new book, The CRO’s Guide to Winning in Private Equity.
JD’s career journey is anything but conventional. Originally a pre-law student, an internship in the Clinton White House shifted his trajectory toward B2B tech sales. His first exit at Intraspect (acquired by Vignette) revealed the thrill of scaling businesses. This spark lit the way to private equity roles, where he helped companies like Motus and BravoSolution achieve phenomenal growth as a CRO. Now, JD is an operating advisor at Five Arrows Capital Partners where he guides 36 portfolio companies through this journey.
Listen to JD's episode on Apple and Spotify.
1. The PE-Centric CRO: A High-Stakes, High-Paced Role
Private equity operates differently than venture capital, and JD likens it to house-flipping for tech companies. It focuses on finding strong foundational elements, driving rapid improvements, and scaling efficiently, all within a tight 3-5 year window. Unlike the longer time horizons of venture capital, PE demands immediate ROI and precise execution. JD highlighted the importance of aligning with the board’s investment thesis from day one and looping back to that vision more frequently than most SaaS revenue leaders. By focusing on a clear value creation plan, CROs can not only meet expectations but also extend their tenure beyond the typical 18 months, which is crucial in PE environments.
2. Annual Planning: Fact, Not Hope
JD’s annual planning philosophy centers on building plans grounded in data rather than optimism. He stresses the importance of starting with historical win rates, ramp times, and attrition rates to project realistic growth. Breaking down annual targets into specific revenue sources such as new logos, cross-sells, and price increases ensures clarity and focus. These targets are then cascaded into achievable monthly goals, providing a roadmap for consistent progress. JD also advocates for leveraging tools like Clari to track performance against leading indicators weekly. His advice, “Inspect what you expect,” underscores the necessity of constant evaluation and course correction.
3. Go-To-Market Design: Structuring for Success
At Motus, JD grew the team from 30 to 200 and restructured the sales organization by segmenting teams into enterprise, mid-market, and SMB groups, with each segment having tailored strategies and success metrics. This segmentation allowed the company to target its Ideal Customer Profile (ICP) more effectively, recognizing that different sales motions require distinct management and operational approaches. JD emphasizes that aligning metrics and expectations with the specific realities of each segment is crucial for maximizing performance and driving growth.
4. Reporting and Inspecting: A Data-Driven Cadence
JD’s philosophy of “Inspect what you expect” is central to his reporting and inspecting framework. He emphasizes the importance of establishing cadences at every level of the organization—from rep-manager to manager-CRO to CRO-board—to ensure alignment and accountability. This process is supported by a robust revenue operations (RevOps) team that automates data collection and generates a weekly flash report, typically on Wednesdays.
This report, spanning just four slides, is shared across sales leadership, the C-suite, and select board members. It tracks all leading indicators laid out at the start of the year, with a horizontal axis representing the weeks of the quarter. By comparing current performance to both the previous quarter and the same quarter last year, the team gains actionable insights. Renewal data is similarly reported.
JD’s cadence extends into meeting rhythms, with early-week one-on-ones focused on forecasting and mid-week flash reports informing strategic discussions on Thursdays and Fridays. This disciplined approach to data and communication fosters problem-solving and ensures that every team member stays on track to meet their targets.
Final Thoughts
To my surprise, JD Miller’s PE approach is highly applicable to the venture-backed world. His playbook from rigorous planning to agile GTM strategies provides a roadmap for CROs seeking to excel in private equity or venture contexts. I would recommend checking out JD’s book, The CRO’s Guide to Winning in Private Equity, which launched yesterday, January 14th.
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