Navigating Trust, Transparency & Transformation: Insights Into Modern Sales Strategies

In other words? Buyers’ expectations are all over the place, and the G2 report posited that it’s due to a lack of trust in salespeople. As sales rep err on the side of reactivity over proactivity, buyers are increasingly returning to self-service options. Chris Heard, CEO of software sourcing platform Olive Technologies, believes this “growth at all costs” mentality is leading SaaS companies to overpromise roadmaps and obscure pricing until sales can position expected value. 

To learn more about the escalating tensions between buyers and sellers, the Demand Gen Report team sat down with Heard to dive deeper into the issue.

Demand Gen Report: How did the world of software become so murky? What are some of the factors that contributed to it?

Chris Heard: Inconsistent software pricing isn’t new, and the rise of agile development in the 2000s exacerbated the issue. This led to incomplete product understanding during the early stages, hindering the creation of clear monetization models for sales teams. The focus on product development resulted in pricing becoming a neglected "product attribute" rather than a dedicated function. 

What hinders software sales today is a dysfunctional system that discourages transparency in pricing discussions. Because pricing remains obscure for buyers, it creates an uneven playing field where similar customers pay different amounts. Sales teams often lack the training on how to discuss pricing openly, which hampers early price conversations.

DGR: Let’s dig deeper into the "growth at all costs" mentality — why is it troubling for businesses and how can sales teams work to move beyond that mentality?

Heard: The "growth at all costs" mentality is often to the detriment of long-term customer satisfaction and sustainable growth. Investors usually prioritize rapid growth above all else, pushing companies to adopt aggressive sales tactics. This strategy leads to a hyperfocus on closing deals quickly, even if it means making misleading promises.

DGR: Why should vendors provide more transparency around software pricing?

Heard: Transparent pricing reduces friction from the buying process and potentially leads to higher conversion rates and faster sales cycles. Transparency also fosters trust between customers and vendors. Knowing precisely what they’re paying for upfront reduces ambiguity and the potential for bait-and-switch tactics. Finally, more transparency about pricing empowers businesses to plan their software budgets accurately, allocate resources effectively and avoid unexpected costs in the future.

Let’s not forget that vendors benefit, too. Transparent pricing attracts customers who are serious about buying and who understand the value proposition, leading to fewer wasted sales resources on unqualified leads. In a competitive market, transparent pricing becomes a differentiator, attracting customers who value upfront information and fair dealings. Customers who understand the value they’re receiving for the price are less likely to churn due to hidden fees or unexpected costs.

DGR: How can salespeople work to generate more trust with prospects? What steps can they take to align?

Heard: During an interaction, salespeople should pay close attention to the prospect's concerns, questions and unspoken cues and ask open-ended questions to encourage the prospect to share their feelings and thoughts openly. This approach helps build understanding and rapport.

You also need to commit to transparency — be honest and upfront about the product or service and share any limitations or potential drawbacks earlier (not later) in the conversation. Listen to prospects’ objections and proactively address them with empathy and clear explanations. Finally, be yourself! Authenticity goes a long way in building trust.

DGR: What are some key sales strategies you’ve deemed successful?

Heard: SaaS vendors should dedicate time to generating and nurturing leads by creating content, guides and webinars that attract and educate potential customers. Companies can optimize content for search engines and relevant topics. Salespeople should actively participate in relevant social media communities, engage with industry influencers and share thought leadership content. The teams should leverage data and insights to personalize cold outreach, ensuring relevance and minimizing intrusiveness.

DGR: In general, how do you see the sales landscape evolving over the next few years?

Heard: More and more sales processes will become automated. The sales process already has more AI applications than most other industries, and while automation helps significantly reduce bias, it will also make it increasingly difficult for companies to stand out.

Branding will become important early on, and many of the trends we see in B2C purchasing — an empowered buyer but with a herd mentality — will become more prevalent in B2B, and larger organizations will thrive. Smaller organizations who haven’t yet established their brand will need to have very clear differentiation, highlighting all that’s wrong with the large organization, like slow to innovate and scale, not trendy, etc.