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Fireside Friday with John Philippo


This is our interview with John Philippo, Sales and Marketing Operations Director at PowerReviews. You can follow PowerReviews at @PowerofReviews.

Sales Assembly: Give us your quick background in sales.

John: My career began in sales but quickly transformed into a sales operations focus. Since moving to sales ops I've primarily worked with companies looking for operational expertise to effectively and efficiently scale their sales team. My responsibilities include everything that goes on behind the scenes to keep sales humming such as analytics, forecasting, system administration, compensation planning, and territory planning.

Sales Assembly: What's your biggest accomplishment in sales or sales leadership?

John: Partnering with Todd Caponi to scale a sales team with a great culture at PowerReviews. When I joined PowerReviews there wasn’t a sales operations function in place and Todd was working to grow and scale the sales team. I’m proud of what the sales team looks like today at PowerReviews and the role I played to get it there.

Sales Assembly: What's the best piece of sales advice you ever got?

John: One of the best things I’ve learned from Todd is that sales reps can get caught up in talking about all the great things their product can do without ever tying it back to what it means for their prospect. As the sales ops director for PowerReviews, I’m consistently meeting with vendors that sell software for sales enablement, analytics, pipeline management, etc. If I have a 30 minute intro call with a rep, and he or she spends the first 15 minutes on a slide showcasing all the logos that they’ve worked with - that rep has already lost me. I am looking for someone who has taken the time to learn about the problems I face and how their solution can directly solve a challenge while providing a strong ROI.

Sales Assembly: What's the biggest challenge facing a sales rep today, and how would you recommend they overcome it?

John: It’s become harder for salespeople to reach decision makers and it’s rarely just about making the dials or logging talk time. Instead, reps must learn about specific topics and pain points that a prospect wishes to learn more about. If a sales rep is given a meeting then they need to come prepared knowing the prospect’s business and its pain points in order to position how their solution can move them forward. Implementing this mindshift in a sales organization can have a significant impact on results for both the sales rep and the businesses they serve.

Sales Assembly: Do you currently have a mentor when it comes to sales, or have you ever? If so, what did they teach you?

John: I'm lucky that Chicago has a strong ecosystem of sales companies which in turn creates a large number of sales operations professionals. I wouldn’t say I have a dedicated mentor but there are a number of people that I share ideas and can bounce ideas around with. But one person who has always been a huge resource for me is Maggie Palumbo who is now the VP of Sales and Operations at Project44. I’ve known her for 10 years and she is always happy to meet for lunch and let me pick her brain. She’s definitely help me grow from being an analyst focused on tactical work to a leader focused on the strategic impact operations can have within a company.

Sales Assembly: What's the best sales book you've ever read? What are you reading now?

John: The best book I’ve read is The Signal and the Noise by Nate Silver. It’s entertaining as it dives into how we have access to more data than ever before, but the true challenge is discerning how to parse out the pieces that are valuable. A book I recently finished and enjoyed was Shoe Dog by Phil Knight. What I really liked about Knight’s memoir is that he is open about the doubt he had growing Nike and the strategies he used to push through it.

Sales Assembly: Best sales or business related articles, podcasts or newsletters?

John: I still really enjoy print and subscribe to a number of different magazines - Fortune, Bloomberg, and Forbes. They all give a good high level overview of trends in the business world with a sprinkling of different political viewpoints.

Sales Assembly: What's the best advice you'd give to someone just starting a career in sales?

John: Emulate the highest performers in the office. Learn what he or she is doing everyday to be successful and incorporate it into your own sales cadence. The other piece is the old adage about “eating the frog.” There are parts of sales that can be hard and uncomfortable when first starting out but it does no good to put it off. Learn to pick up the phone and deal with hearing the word 'no.'

Sales Assembly: Do you see any interesting future trends as it pertains to sales?

John: AI and automation will become a bigger and better resource for sales as the technology improves. The companies that learn how to best leverage the technologies that allow salespeople to focus on high value activity (building relationships) will be the most successful.

Sales Assembly: How do you see sales operations changing in the future?

John: 10 or 15 years ago, sales operations barely existed and only the most forward thinking sales organizations recognized it as a valuable function. In the future I think the breadth of responsibilities of the sales ops team expand beyond the traditional sales silo to become more of a revenue operations role. Many SaaS companies here in Chicago are already seeing the value of a Chief Revenue Executive. Sales is no longer viewed as a separate entity with no impact on other business functions because marketing, sales, client success, renewals, etc. are all linked to the lifecycle of a client. A revenue operations team with responsibility in supporting all of these business functions will be the next step in the sales operations arena.

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