Software Sales Tips by Matt Wolach

Scale Your SaaS

VIDEOCAST: How to Market Large Enterprises – with Tim Whiting


Tim discusses the ins and outs of marketing large enterprises with Matt Wolach, the host of SaaS-Story in the Making Podcast. Tim masterfully dissects the differences (in scale and requirements) between marketing enterprises and marketing small and medium-sized businesses.

While sharing the current top marketing tactics for engaging enterprises’ customers, Tim touches on the sales and marketing intersect and the importance of having a synergy between sales and marketing. Tim also talks about the science of in-depth data analysis and the art of using analyzed data to customize for different categories of customers.


Podcast: SaaS-Story in the Making

Episode: How to Market Large Enterprises

Host: Matt Wolach, a B2B SaaS sales coach, Entrepreneur, and Investor.

Guest: Tim Whiting, VP Marketing at Label Insights, the world’s leading product attribute metadata solution.


Make Data Your Bow

Big data and large enterprises are inseparable. Success at marketing large enterprises hinges on how well data is utilized. Tim offers a framework for fetching, analyzing, and utilizing data.

When dealing with enterprises, Tim advocates tapping into the DNA of a large cross-section of products to discover market trends, uncover market variables, and bring to bear unknown factors driving success in different sections of the market.

Tim thinks that the best way to fetch data in a large market is to do what he calls “ingredient analysis” on the implicit and the explicit features of products.

After actionable insights have been gained from gathered and analyzed data, data can then be used to educate customers on the existence of a problem and to then to show value.

For Every Prey, Shoot Differently

Large Enterprises attract a large customer base. A large customer base means you are dealing with a lot of sophistication, a lot of demographic and psychographic variety.  Large Enterprises have customers that cut across different spectra of needs, maturity, and strategic imperatives. Enterprises are beleaguered with customers who do not want to fit into a category, customers who want to be treated as distinct entities, customers who want you to show that you understand them.

As such, customizing for these customers is hard. Having made data your bow, Tim advises that you should use gathered and analyzed data to spin content in different ways to different kinds of customers. You should reach out to audiences from different angles. You should build trust by crafting your marketing narrative to suit each set or subset of customers.

Optimize Your Pitch Deck

As simplistic as it may sound, the pitch deck is one of the most trusted tactics to weigh the impact of a marketing narrative. A pitch deck helps you craft your narrative to educate customers, bond better with customers, and build trust.

As much as a pitch deck works for enterprises’ customers, it has to be optimized. The marketing narrative has to be centered on knowing the customers’ problems and the challenges that could exist whilst trying to solve them.

Optimizing the pitch deck helps you hone your message and tailor it so it starts triggering the right behavior, Tim says.

Be Ready To Expand

It is the dream of every startup to scale and accelerate into a large enterprise. Tim advises that while companies should focus on landing or closing deals, attention should be paid to the prospect of an expansion.

Tim thinks that companies should devote a portion of their resources to expansion and renewal. Tim says it is better to develop workings in anticipation of an expansion than to work with ad-hoc schemes.


Switching an Enterprise for a Startup? Find a Bridge

“I started with larger enterprises and that has both a positive and a negative effect. On the positive side, you can get an understanding of what greatness looks like with the structure and workings of larger companies. On the flip side, working with large companies carries a stigma. There would be doubts that you might not be able to work at the pace of startups.”

“If you work with a larger company and you seek to be in a startup, find a functional bridge, or a category that gives you credibility.”

A Pitch Deck is Your Best Bet

“A great tactic to craft your narrative and to understand if the narrative is resonating is a pitch deck. It is hard to get your story crafted in a way that not only educates and creates awareness but starts to build trust without a pitch deck.”

“The pitch deck you might be using to raise money and educate investors is not the same narrative you are going to be using with an enterprise customer. The narrative has to be built around knowing the customer’s problems and the existing big challenges. The pitch deck helps you hone your message and tailor it so it starts driving the right behavior.”

Mass Customization is a Dream

“You cannot have one story that would resonate across a category and an industry. There is such a spectrum of maturity amongst customers, such a spectrum of what their strategic imperatives are, such a spectrum of the type of individuals you are speaking with.”

“With enterprises, people do not want to be treated as a general category, they want to be understood as a specific enterprise and they want you to demonstrate that you understand them.”

Small and Mid-sized businesses versus enterprises

“With larger enterprises, there are a smaller number of larger dollar opportunities coming to individuals; the number of available prospects is limited and this calls for a thoughtful, organized, and strategic synergy between sales and marketing.”

“Within these large enterprises, you have vast and large buying groups and complex buying cycles which require a different approach.  With enterprises, you have longer sales cycles, complex buying cycles, a huge chunk of resources spent in procurement and negotiation, a lot of anticipation and pro-activity, and a lot of landing and expansion strategies playing out.”



[03:57] “The power in any type of technology is the data that drives it.”

[05:55] “The way to understand business is to go into sales but [06:15] the scale of value will come from marketing.”

[13:30] “Build your narrative around knowing the customer.”

[15:00] “You cannot have one story that would resonate across a category and an industry.”

[21:38] “Marketing enterprises involves a lot of organization, and a strategic synergy between sales and marketing.”


To learn more about Tim Whiting and Label Insight, visit: 

You can also find Tim Whiting on LinkedIn at    

For more about how host Matt Wolach helps software companies achieve maximum growth, visit                                               

As part of the founding team in his first SaaS product, Matt owned the sales & marketing processes. But he struggled to sell and gain traction for the company. It took years of learning and tweaking before Matt created The Perfect DEAL Process, an innovative yet easy to implement method for closing more software deals. To find out more, visit

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