Modernizing the Sales Process
Sales Management 06.27.2023

Modernizing the Sales Process

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In this episode of Sunny Side Up, host Katherine Noonan interviews Mike Head, the Chief Revenue Officer at, discussing the revolutionization of sales strategies and best practices for modernizing the sales process. The conversation highlights several key takeaways, including the importance of delivering a delightful customer experience and meeting buyers where they are in the information-rich landscape. They emphasize the value of transparency in sales, being open about both strengths and limitations and leveraging unbiased third-party information to guide buyers. The discussion also explores strategies for navigating risk-averse buyers, aligning solutions with strategic priorities, and adapting to the current economic environment. Mike also discusses adapting messaging and positioning in uncertain times, including CFOs in the process by speaking their language, understanding customers’ persona, and aligning products or solutions to their problems.

About the Guest

Mike Head is an accomplished executive with a strong background in revenue generation and strategic partnerships. Currently serving as the Chief Revenue Officer (CRO) at, he is responsible for driving overall global revenue growth for the organization. During his tenure as the Chief Partnerships Officer at, Mike played a vital role in the company’s growth journey, starting as an Account Executive and progressing to the Senior Leadership team. He worked across all go-to-market functions, building teams and partnerships, shaping strategies, and contributing to exceeding $100 million in annual recurring revenue (ARR).

Connect with Mike Head

Key Takeaways

  • Emphasizing the customer experience and adapting to the evolving buyer landscape.
  • Leveraging transparency and openness to build trust and credibility.
  • Utilizing third-party information and unbiased reviews to guide buyers.
  • Adapting sales strategies to address the challenges posed by risk-averse buyers.
  • Aligning solutions with the strategic priorities of the company and its executives.
  • Navigating the current economic downturn by refining messaging and focusing on key metrics.
  • Incorporating CFOs into sales processes and speaking their language.
  • Highlighting the importance of understanding company strategic priorities.
  • Leveling up conversations to tie persona priorities with strategic objectives.
  • Aligning solutions with top-line initiatives for increased success.
  • Increasing CFO involvement in vendor contracts and scrutiny on single vendor line items.
  • Adapting sales approaches to address evolving CFO engagement.
  • Recognizing the value of strategic partnerships in driving revenue growth.
  • Focusing on revenue generation, building teams, and shaping sales strategies for success.
  • Taking risks to drive growth is no longer the primary focus in the current economic climate. 
  • The sales process should uncover pain points and make sure recommendations are specific and actionable. 
  • Multi-threading is important to understand the concerns and priorities of any given company. 
  • Messaging and positioning must be adapted to the times, with an emphasis on profitability, payback periods, customer acquisition costs, etc. 
  • CFOs are more involved in decision-making, so communication must be leveled up.


“It’s all about the buyer. It’s all about the customer experience. If you can deliver a delightful experience for the customer that both get some of the information that they need and helps them see a new way of doing business, you create wins for everyone involved.”  – Mike Head

Highlights from the Episode

Can you share some insights on the work that you guys are doing as a team that you’re particularly proud of?

Mike shared that they are bringing new products to the market, focusing on processes and rev ops enablement to prepare for the launch of a second SKU. They have also reintroduced the curiosity-driven approach to their team, which has received positive feedback from both buyers and sellers. Additionally, they are focused on the coaching methodology called Med Pick, which has proven to help their AEs be more successful.

What drives your passion for modernizing the sales process? Can you share insights on the key elements of a successful modern sales approach?

Mike’s passion for modernizing the sales process is rooted in its commitment to delivering a delightful customer experience. He emphasized that customer satisfaction is paramount and achieving that requires meeting buyers where they are. With the abundance of information available, their goal is to provide buyers with the right level of unbiased information to make informed decisions. One key element of a successful modern sales approach, according to Mike, is embracing transparency. They focus on being open and honest about their strengths and weaknesses as a vendor, as well as making recommendations based on the buyer’s specific needs. They also leverage B2B reviews from platforms like G2 to gather valuable feedback and incorporate it into their sales process. Another important strategy they employ is providing buyers with third-party articles and content to ensure they have access to unbiased information throughout their journey.

What strategies are you implementing to help modernize your sellers today given the availability of information?

Mike outlined several strategies they are implementing to modernize their sellers in light of the availability of information. Firstly, they are embracing transparency and openly discussing both their strengths and weaknesses as a vendor. This approach builds trust and credibility with buyers. They also leverage B2B review platforms like G2 to gather feedback and incorporate it into their sales process, highlighting both positive aspects and concerns raised by customers. Additionally, they focus on providing unbiased information to buyers by sharing relevant third-party articles and content. They also aim to control the flow of information by not just sending information about themselves but also guiding buyers to access unbiased information that helps them make informed decisions.

How do you adapt and make changes to your sales process to address challenges posed by very risk-averse buyers?

Mike acknowledged the challenges posed by risk-averse buyers and outlined their approach to address them. Their goal is to provide buyers with a sense of confidence and assurance that their decision to select their solution will lead to success. To achieve this, they focus on understanding the specific pain points of buyers and making recommendations that are specific and actionable. They ensure that their solutions come with the necessary support, whether through professional services or agencies, to help buyers achieve the desired outcomes. Additionally, they recognize the importance of engaging with all stakeholders involved in the decision-making process, particularly in enterprise sales and understanding their concerns and priorities. By addressing these concerns and aligning their solution with strategic priorities, they can instill greater confidence in risk-averse buyers.

How is your organization navigating the current economic downturn or the current environment?

Mike discussed their approach to navigating the current economic environment. They are fortunate in that their solution performs well in uncertain times since their customer acquisition campaigns are tied to specific outcomes that businesses care about. They refine their messaging and positioning to align with current market conditions, focusing on metrics such as mis litigation, profitability, and key metrics that CFOs care about. They also emphasize effective communication by speaking the language of CFOs and addressing their specific concerns. Additionally, they recognize the importance of understanding the strategic priorities of companies and how their solution can support those priorities. By tailoring their approach to these factors, they can continue to thrive and provide value in the current economic climate.

How have you seen the CFO persona evolve in terms of their engagement with sales cycles?

Mike explains that there has been a notable shift in the engagement of CFOs with sales cycles over time. CFOs are now actively involved in both existing customer relationships and new growth opportunities. One significant aspect of this change is that CFOs are increasingly focused on vendor contracts and closely examining individual line items to identify potential cost reductions. This means that sales professionals need to be prepared to address these concerns and demonstrate the value and efficiency of their offerings. Furthermore, CFOs are playing a more prominent role in approving overall contracts, particularly those related to marketing budgets. While sales professionals previously had more flexibility in utilizing these budgets, they now face an additional layer of scrutiny and require CFO approval before finalizing deals.

Has engagement with CFOs affected the selling process?

The increased involvement of CFOs in the sales process has indeed impacted the way sales professionals operate. In the past, they had more freedom and autonomy in utilizing marketing budgets without needing explicit approval from CFOs. However, with the evolving landscape, the engagement of CFOs has introduced an additional challenge. Sales professionals must now navigate the scrutiny of CFOs, address their concerns regarding vendor contracts and cost reductions, and secure their approval before finalizing deals. This additional layer of approval has made the selling process more complex and requires sales professionals to adapt their strategies and approaches accordingly.

How does this increased scrutiny impact the selling environment?

The heightened scrutiny from CFOs has undoubtedly transformed the selling environment. However, Mike perceives this change as a significant opportunity for sales professionals. In the current climate, where CFOs are closely scrutinizing contracts and demanding cost reductions, sales professionals have the chance to excel by focusing on the fundamentals of their craft. This means honing their skills, refining their strategies, and practicing diligently. While the growth cycles of the past allowed for relatively easier success, thriving in the current environment requires sales professionals to think differently and approach deals from a fresh perspective. Mike emphasizes that succeeding in this challenging selling environment demonstrates adaptability and proficiency, setting up sales professionals for success in any future market conditions. It’s an opportunity for them to refine their abilities and develop a resilient mindset that can withstand the cyclical nature of business growth.

Is there a book, blog, newsletter, website, or video that you would recommend to our listeners?



Matthew Dixon – Author and Founding Partner at DCM Insights

Chris OrlobCEO at

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