As Heads of Sales, many of us started our sales management careers as first-line sales managers. I would argue that this critical role is the hardest and most underappreciated in the field force. Today, first-line sales management still lacks adequate tools:, in a rapidly evolving sales landscape, current tools fall short in aiding sales managers' strategic decision-making. First-line sales managers have not benefited from current sales productivity, data analysis, and visualization tools as much as executive sales management, revenue/sales ops, and individual contributors have. The challenges I faced along my journey display the need for AI-based solutions.
My experience highlights the struggles of managing teams effectively and how a lack of visibility hampers growth.
In this series of three blog posts, I will share:
- The understated challenges first-line sales managers face based on insights from my career journey.
- How I think the current tools we have implemented to cope with the increasing volumes of data do not adequately help sales managers.
- How AI-based tools can create the opportunity to properly support managers.
My Sales Journey:
Regional Manager (RM) Role:
In 1987, I was promoted to my first sales management role as Regional Manager (RM) Northeast for an enterprise software company (Thorn EMI Computer Software). Like many others who moved from a sales role into the RM role, I brought with me a limited relevant skill set. The skill set I had comprised of prospecting for leads, making cold calls, presenting the product, handling objections, and hosting sales meetings with potential customers. However, these qualities were only a small part of my new job. It took me three to four painful years to learn the job, and I can honestly say that those years were the hardest of my career. I can admit—many years later—that I missed my numbers and had an unacceptable turnover rate among my sales representatives.
Managing and growing a team was challenging. I needed to learn how to hire, retain, guide, and motivate people. Although I had the skills to manage my own pipeline, I had to learn how to ensure that my sales representatives, who had varying skill levels, had sufficient pipeline and were following a prescribed sales process. Additionally, I had to provide quarterly forecasts and assess my team’s progress for higher levels of sales management. The actions that I needed to take to set my team up for success were more foreign than familiar.
Even when I became successful—regularly hitting my numbers and making consecutive President’s Clubs—I often had a smaller W2 than many of my sales reps. However, this served me as an apprenticeship and gave me the opportunity to join Informatica (INFA), their first sales hire as VP Sales in 1995, when it was just a 12-person company.
First Head of Sales Role:
One of the big lessons I learned at Informatica was that unless I was paranoid about making my first-line sales managers successful, we would miss our sales targets. During 1995, I hired salespeople to manage East, West, Central, and South for North America. My experience as an RM enabled me to hire, motivate, and manage a great group for a successful 18 months. After our second round of funding, we hired territory sales managers in New York, Los Angeles, and Chicago. Although our success continued, as I was able to work with my original team to help them develop their management talents, the team felt like it was becoming loose knit and beginning to somewhat unravel.
The challenges really began a year before we went public when my original team had to hire their own RMs to run areas (e.g. we needed an RM for the Northeast to manage reps in Boston, New York, Philadelphia, etc.). Looking back on this period we managed our way through this somewhat due to the momentum of our sales engine and the market was hot for our product. But we had to replace too many newly hired or promoted RMs. At this size, as CRO, I wasn't engaged in working directly with reps or RMs;I lacked visibility into their sales processes to be able to support my direct management team in making the necessary changes. Lack of visibility into this black box of deal flow through management levels is one of the main reasons I think many companies fail to grow and fail too early. This lesson was key in understanding that efficiently focusing on my first-line sales managers is foundational for success.
CRO in the High-Velocity Selling World:
Informatica IPO’d in 1999 and we grew it to be a successful public company which I left in 2005. After spending several years working as a Social Enterprise Director focused on helping youth in East Oakland, I returned to software sales at Jaspersoft as CRO in 2012. The software sales world had changed dramatically between 2005 and 2012. Jaspersoft was based on an open-source subscription-based business model. The open-source model and average selling price required a far higher velocity cadence (many smaller deals) than the large perpetual enterprise sales pace I was used to. With this model and the advance of data collection came an enormous amount of data. Sales Operations at Jaspersoft provided me with a comprehensive data warehouse with fields ranging from demo downloads to all stages of pipeline progress to renewal details. I could build dashboards to track individuals' performance, forecast progression, and resource levels. Having an Operational Research degree and having sold analytics tools for many years, I had a passion for data and managed to swim in the tsunami of information I faced. But I always felt I might be just treading water, and I certainly saw many of my managers sinking in the overload. Visualization of data is not the same as providing guidance—the tools I used did not help integrate insights into broad sales strategies. I will discuss this more in my next blog.
Next Blog:
In my next blog post, I want to examine why the current tools provided to sales managers have not necessarily improved their ability to predictably grow profitable revenue. While these tools can certainly benefit individual sales reps by improving their efficiency, organization, and effectiveness in engaging with prospects, they do not offer the same level of strategic oversight and coordination that sales managers require to optimize team performance and achieve broader sales objectives.
