This is Part 4 of sales and marketing alignment blog series based on conversations with Insightly VP of Sales Mark Ripley and CMO Tony Kavanagh.

In 3 Ways to use data for sales and marketing alignment, we explored why data is the cornerstone of effective sales and marketing alignment and how to use data to align the teams. However, data has minimal value if your sales and marketing leaders are misaligned.

Based on my recent conversations with VP of Sales Mark Ripley and CMO Tony Kavanagh of Insightly, here are a few best practices for creating alignment between sales and marketing leaders as well as a look into why sales and marketing team misalignment is so common.

Why sales and marketing misalignment is common

If you surveyed a random sample of sales and marketing leaders, you would likely receive a broad spectrum of opinions about alignment in their organizations. After all, merely defining sales and marketing alignment can yield more frustration than clarity. Yet, most leaders still prefer alignment to misalignment; but only few know how to make it a reality.

Why is the alignment equation so difficult to solve? For starters, it’s hard to ignore the differences in skills, abilities, work patterns, and personalities that are unique to each leadership role.

“Sales and marketing leaders can be different animals, even though they usually have more in common than they might think,” says Mark, VP of Sales at Insightly.

Strong demand for executive-level talent combined with high turnover rates have accelerated misalignment at many organizations. In an era when the average executive spends five years or less working for a given company, some leaders are reluctant to invest time and effort on learning new ways to connect and build long-term alignment with their colleagues and teams.

No doubt, there are many factors that cause misalignment among leaders. Unfortunately, this problem doesn’t correct itself organically from the bottom up. Rather, true alignment requires a long-term perspective that starts at the top.

“To achieve lasting alignment that produces meaningful results, you need a firm commitment from everyone at the leadership level,” says Tony, CMO at Insightly.

People don’t enjoy feeling frustrated at work. Yet, when sales and marketing leaders aren’t in total alignment, frustration becomes a very common reality. And, regular meetings and updates are not enough to build a true alignment and make progress on goals.

At Insightly, Mark and Tony figured out that in order to make their regular meetings and data sharing more useful and avoid frustration, they needed to align their teams around a shared set of objectives, methods, and metrics.

Developing objectives, methods, & metrics

Seeking a fresh perspective, Mark and Tony decided to hit the reset button and revisit the company’s broader goals. Based on previous strategic planning sessions, both leaders knew where the company wanted to be within the next three years. Using this shared vision as their guide, the two worked together to identify strategic initiatives for the year ahead.

“We both agreed on the company’s top goals for the organization,” says Tony. “This alignment allowed us to take the next step, which involved creating objectives, methods, and metrics.”

Insightly uses objectives, methods, and metrics to break annual goals into quarterly initiatives for each department. The company defines these terms as follows:


An objective is a two or three-word statement that explains what the department aims to accomplish within a defined period.


The method explains how Insightly will reach a given objective. Although brief (three to four sentences), the method needs to provide a specific and actionable explanation of key initiatives.


A metric provides the measurable definition of success for a particular objective. Metrics are best expressed as quantitative data points.

For example, “going outbound” is a top priority for Insightly’s sales team in 2019. By using the objective, method, and metric model, the sales team crafted a concise plan of action to provide clarity for both departments.

“Our method explains how we plan to achieve the objective during the first quarter, and our metrics are based on a number of appointment bookings and opportunities from outbound,” says Mark.

Gaining buy-in

Simply developing high-level objectives, methods, and metrics is no guarantee for alignment. Before anything is operationalized at the department level, leaders must first gain buy-in from their counterparts.

“Gaining buy-in is the most important piece of alignment between sales and marketing leaders,” says Tony. “This process can require significant negotiation, discussion, and refinement to achieve a set of shared objectives that everyone can agree on.”

So, what’s the best way to ensure leaders understand and agree on one another’s objectives? At Insightly, the leadership team uses offsite meetings to facilitate open and candid conversations.

“During the offsite meeting we discuss each department’s objectives, methods, and metrics,” says Mark. “The point of the meeting is to identify overlap, make adjustments, and align on priorities for the next six months.”

By creating a shared understanding of objectives, methods, and metrics, leaders walk away from the offsite meeting feeling energized and confident about the months ahead.

“Aligning on big picture goals improves marketing’s ability to support the sales team and their objectives,” says Tony. “Sales also gains a solid understanding of where the marketing group is headed and the feedback we need to achieve our goals.”

Next up: Operationalizing alignment at the department level

Stay tuned for our next post where we will discuss how to convert alignment at the leadership level to the rest of the organization. We’ll also explore how Insightly is leveraging business intelligence and data analytics to foster greater alignment among cross-functional teams.

In the meantime, check out our previous posts on sales and marketing alignment: