Welcome to Mavens of Modern Sales, where we take a deep dive with the sales leaders pulling sales teams in the 21st century to get their insights on leadership, strategy, industry trends, and more.
This week we talked to JD Miller, Go-to-Market Operating Advisor for Five Arrows Capital Partners.
You recently mentioned that you believe most CROs aren’t let go for missing quota, but for missing forecasting targets. Do you have any advice or strategies to narrow the miss for forecasts?
While we always want CROs to hit their quota, I definitely believe that their tenure is more directly tied to their ability to forecast accurately, regardless of the number called. When a new CRO takes over, especially after a period of underperformance, the leadership team needs confidence and visibility. They’re willing to accept a potential miss, but they need to understand the trajectory and timeline for improvement.
Accurate forecasting gives the organization the crucial gift of time. It allows them to adjust budgets, reallocate resources, and make strategic decisions to navigate the anticipated gap. Surprise misses, on the other hand, lead to reactive and often drastic measures like layoffs, which can damage morale and long-term growth of the company.
In my experience, the most effective forecasting combines data-driven insights with human judgment. AI tools are incredibly powerful for analyzing historical deal data and identifying patterns. I’ve seen firsthand how AI can forecast quarterly results with remarkable accuracy – in one company I worked with, it achieved 2% margin of error by the second week of the quarter, for 16 out of 17 quarters where we used the tool.
However, while AI provides a high-level view, it’s equally important to develop a robust forecasting process within the sales team itself. I implement a system where each seller categorizes their deals as “committed,” “best case,” or “unlikely,” along with estimated close dates and values. Sales managers then review and provide their own forecasts. By tracking this weekly, we gain valuable insights into individual forecasting tendencies.
This process allows us to identify who tends to be overly optimistic, who underestimates their pipeline, and where common forecasting errors occur. This data is crucial for coaching and developing the team’s forecasting skills, leading to more accurate predictions and better overall sales performance.
We’ve heard you talk about building a brand as an executive and you recently shared 6 tips for crafting a personal brand story. Why do you believe it is important for executives to have a strong personal brand?
As an executive who has made his career in private equity, I’ve tended to see jobs in short stints. A company changes ownership, I get hired to run sales for a period of up to five years, and the PE owner sells the (hopefully better) company to a new owner who will run the cycle again.
The data tells me my experience isn’t unique. College graduates are anticipated to have over a dozen jobs in the course of their professional career – and the average tenure of most CROs is a short 17 months.
While we must be strong ambassadors for our current employers, it’s equally crucial for executives to cultivate our own brand. A strong personal brand communicates our unique value proposition, showcases our expertise, and builds credibility beyond any single organization. It’s about owning our own narrative and ensuring it resonates with our future aspirations.
For me, personal branding has been a continuous journey. I’ve actively engaged on LinkedIn, participated in industry events, written articles, and sought opportunities to share my insights in written publications. I’m fortunate that I genuinely enjoy doing all of these things. But I also recognize that even if an executive doesn’t, they’re not optional – the more I invest in my personal brand, the more opportunities present themselves.
Enablement is taking a lot of heat recently. Late last year you spoke with the Revenue Operations Alliance about how important it is for CROs to partner with enablement quickly. Can you share why this partnership is so important and what both parties should be focused on to make sure impacts are measurable for each?
Enablement is absolutely critical for driving consistent sales performance, and I’m surprised it’s receiving criticism. Leading a sales organization, especially one with hundreds of go-to-market professionals, requires more than just setting a strategy. It demands effective communication, training, and ongoing support to ensure every individual contributor understands and executes that strategy successfully. And that’s way more work than any single sales leader can do on their own. That’s where enablement shines.
A strong enablement team acts as a force multiplier, translating strategic vision into tangible results. To achieve this, close collaboration between the CRO and enablement leader is vital. In my experience, this involves shared understanding of the strategic goals, key performance indicators, and a regular cadence of review and course correction.
A few years ago, I implemented a new sales methodology, based on a nine-question framework. We knew that simply introducing it at a sales kickoff wouldn’t be enough. So, we adopted a data-driven approach to enablement. Each month, we analyzed closed deals, identifying which of the nine questions were most frequently missed in lost opportunities. This insight informed our training focus for the following month. By delivering targeted, just-in-time training based on real-world data, we saw significant improvements in sales results.
This example highlights the power of aligning enablement with strategic priorities and leveraging data to drive continuous improvement. When done effectively, enablement becomes the engine that drives sales performance and ensures everyone is equipped to succeed.
You’ve been an instructor for a C-Suite Masterclass. For the readers who are Individual Contributors but have dreams of being a part of the C-Suite, what should they be doing or focusing on to gain the skills to be a successful leader in the future?
Moving from individual contributor to C-suite leader requires a shift in mindset and skillset. Many talented individual contributors stumble when they first step into leadership roles because they try to replicate their individual success by becoming “super-contributors” who micromanage and take over tasks, rather than empowering their teams.
To truly excel as a leader, you need to evolve beyond individual contributions. Here are some key areas to focus on:
- Develop your coaching and mentoring skills: Identify what made you successful and translate those skills into effective coaching strategies. Focus on empowering others, providing guidance, and removing obstacles to their success.
- Embrace delegation and trust: Learn to delegate effectively and trust your team to execute. It’s scary to give up control, but you’ll never be able to lead a team of any size if every deal and every person’s success is dependent on you. Trusting others is crucial for scaling your impact and creating a high-performing culture.
- Shift your focus from “me” to “we”: As a top-performing seller, you are probably used to getting all sorts of attention, rewards, and recognition. As a leader, this focus has to shift – your success is measured by the collective achievements of your team, and you need to become the one showing attention on your team members. Celebrate their wins, provide support during challenges, and shine the spotlight on their accomplishments.
- Cultivate emotional intelligence: Develop strong self-awareness, empathy, and interpersonal skills. As a leader, I’m someone that everyone in the company has an opinion about. Some may be good, most are neutral, and some may be highly critical in public forums like Glassdoor or company meetings. Understanding how I’m perceived by others, not taking things personally, and adapting communication styles to fit how my audience will best hear my message is critically important.
- Become a strategic thinker: Sometimes what’s best for you as an individual contributor is not what’s best for your team or company. Expand your perspective beyond your immediate role and develop a deep understanding of the business, the market, and the competitive landscape.
Seek out leadership opportunities: Volunteer for projects, lead initiatives, and actively seek opportunities to demonstrate your leadership potential.
You were previously the President of the Board of Directors for Care For Friends. It’s clear this organization is important to you. What inspired you to get involved with volunteer work and why do you believe it’s important for professionals, especially those in leadership positions, to dedicate their time to causes they care about?
I’ve been incredibly fortunate in my career, achieving a level of success that comes with both professional recognition and financial rewards. But I also recognize that my road to this success was paved with advantages – a supportive family who prioritized education, a community rich with opportunities, and mentors who guided me along the way. Not everyone has that same good luck.
My involvement with Care For Friends, an organization dedicated to supporting individuals experiencing homelessness, has been a profound experience. It’s opened my eyes to the systemic inequalities and challenges faced by those who haven’t had the same opportunities. It’s shown me that many individuals experiencing homelessness possess the same drive, intelligence, and work ethic as anyone else. They were simply dealt a hand that put them in a different starting place than I had.
There’s a line in the musical Hadestown that says “if everyone takes only what they need, there will always be enough.” I believe those of us who have been given way more than we need have an obligation to give back and create opportunities for those who have never had access to enough. For professionals, especially those in leadership positions, dedicating time to causes we care about is more than just charity – it’s an investment in our community and a chance to make a tangible difference.
JD Miller is a Go-to-Market Operating Advisor for Five Arrows Capital Partners. He has consolidated his experiences from over 25 years of B2B Tech Sales experience in his book “The CRO’s Guide to Winning In Private Equity,” which will be released on January 14th, 2025. More details at www.jdmillerphd.com/book
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