SalesTechStar Interview with Ryan Whitney, Chief Sales Officer at AnyRoad

Ryan Whitney, Chief Sales Officer at AnyRoad caught up with the team at SalesTechStar for a short discussion on what it takes to scale and train sales teams to optimize buying experiences and overall sales ROI;

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Hi Ryan, we’d love to hear about your journey through the years…what made you venture into sales?

My father was in sales his entire career and I witnessed his journey as I grew up. He instilled in me the work ethic, persistence and perseverance you need in sales, along with autonomy and flexibility to chart your own path.

My first sales job was managing the PNW region for a medical device company, selling a cardiac heart monitor to cardiologists, hospitals and medical facilities. The job taught me how to cold call, prospect and tell a quick-value story to a very busy physician. After three years of being on the road 100% of the time, I decided it was time to venture into the software/IT space. I joined a staff augmentation/project management company as a business development director on a team that opened new offices & markets and broke into new industries.

In 2003, I joined ServiceSource as employee #45 to help them create the category of “outsourced renewal management” and grow revenues from <$10M to a successful IPO in 2011 with a global footprint. I started the company’s healthcare division in 2007 and sold our solutions globally. This role gave me experience in scaling a business and meeting the growing demands of revenue generation through a new solution.

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In 2013, I joined Gainsight to help create the category of “customer success management” and break into the enterprise. I moved into management in 2015 and led the North America Enterprise sales team. Over a seven year period, we grew revenue from $1M to $100M and earned a successful strategic investment by Vista Equity that valued the company at $1B. I ran every sales team and function during my tenure and helped create new markets and customers globally.

Earlier this year, I joined AnyRoad as the Chief Sales Officer to help build and define the “experience relationship management” (ERM) category. ERM is a new category of software meant to reflect the intersection of CRM and experience data. AnyRoad helps brands measure, scale and implement their online, offline and hybrid branded experiences – and it’s an incredibly exciting time as the world is experiencing a post-pandemic experience renaissance.

What does it take to scale sales processes for startups as they expand in your view and what are some best practices startup sales teams should follow when scaling?

The first step for any successful sales team is defining a sales process that’s repeatable, based on experience in the market, and documented over a period of time. That process can be continuously optimized as the company grows and gets better at defining the stages of a sale or smarter about the profiles of different potential buyers.

It’s also important to think about the sale from a buyer’s lens and understand what it takes for the prospect to buy and secure the solution, and then map that back to your own sales process so it becomes collaborative.

We take this buyer-centric approach at AnyRoad. Our sales strategy takes into account what our customers are trying to solve for, what they are trying to buy and which pieces of their organizations need to be involved in the process. With that in mind, we continuously optimize our sales process to be more efficient, effective, repeatable and scalable as we continue to hire and we’ve found that common definitions with common frameworks is helping drive our success.

What are some top factors that you feel a sales leader needs to address when training, hiring and building out a sales team?

Hiring managers should look for diverse backgrounds and skill sets that complement what they are trying to achieve within their sales organizations. Too many leaders try to hire for the exact same profile and that restricts the team’s ability to learn from each other. The main attribute I look for in new hires is a curious mindset, which points to their ability to ask good questions and advance discussions, and their diverse experiences and approaches are icing on the cake.

I am a believer that just because you, as a manager, have sold one way doesn’t mean that it’s the absolute right way. If you are trying to have all your AEs work in the same way, it will only frustrate them, hinder creativity and limit the number of closed deals. The most successful sales teams come from different backgrounds, encourage new ways of thinking, and take tailored approaches based on personality and learning styles. We can all work toward the same goal but get there in different manners–there is no one-size-fits-all approach to sales.

As businesses start to reopen from the effects of the pandemic lockdown (still in part at the moment) what are some back to office sales tips you’d highlight?

What often gets lost in the remote work environment is the personal connection. It’s easy to get on a call (with team members or prospects) and get right to the point and only talk business.

Whether you are already back in the office, working in a hybrid setting, or staying remote forever, my advice is to work hard to connect with colleagues, peers, and clients on a personal level. How? Get off Zoom 24/7. Ask your team questions about what their career goals are or how they are doing in general. Find ways to have fun as a group, whether virtual or in the office.

Building relationships is particularly important at startups because having a sense of community helps teams get through trials and tribulations (which are evident in any early-stage company).

How do you feel sales platforms and sales technologies will evolve in future and what will drive demand for more innovations and what kind?

Technology is becoming increasingly important in sales, especially with the rise of the remote workforce. Remote team management and enablement platforms, such as Gong, Seismic etc., will play a key role in helping sales teams succeed even after the pandemic subsides.

Insights platforms, like ZoomInfo and Emissary, which already help AEs improve personalization, and forecasting and deal management solutions, such as Clari, People.ai and Datahug, which are becoming much more scientific with AI and ML capabilities, will get even more advanced.

Sales professionals can also expect to see more intelligence in workflow-related applications/solutions, such as Troop and Slack, that will provide even more usability to sales and go-to-market teams in the future – where the technology guides, directs and alerts you of information that will be helpful in the sales process. Think of it like Siri but for business.

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A few thoughts on what you feel today’s sales and marketing leaders need to do differently to build unique buying experiences?

 The most important thing for standing out from the crowd is knowing and understanding your customers. Leaders must connect directly with customers by joining sales calls and QBRs and through programs like executive sponsorships. Taking this direct connection and combining it with better customer insights through surveys, sales intelligence and customer references is key to a successful sales operation.

AnyRoad, just like other enterprise software companies, has a highly flexible platform and by having a better understanding of our audience, we can take a consultative process to the sale and ensure we can deliver exactly what our customer needs. Again, sales is never one-size-fits-all.