• Sales Assembly

Fireside Friday with Howard Diamond

This is our interview with Howard Diamond, Chief Strategy Officer at Rise Interactive. You can follow Howard at @HDRise.

Sales Assembly: Give us your quick background in sales:

Howard: More than 20 years of sales experience from selling promotional specialty items (HA-LO) and newspaper ads (the Daily Illini) in college to a number of successful Chicago based technology companies including Coolsavings.com, Coe Truman and Rise Interactive. I have been fortunate to work with many smart technology and business leaders helping to scale organizations through a heavy investment in sales strategy and infrastructure.

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

Howard: Being part of the coolsavings.com growth from 6 figures to 8 figures in revenue in 2 short years. Growing Rise Interactive from 8 to 250 employees.

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

Howard: I would not have had any success at all if it weren't for all the coaching and mentoring I have had over the years. Nancy Elliot, the advertising manager at the Daily Illini had an incredible impact on me in terms of selling strategies. One thing I always remembered is that if you create a spec for a prospective client, and they ask you to make changes, you have effectively made the sale! Do spec work...

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

Howard: There is a lot of noise out there. Anyone with any kind of budget is being contacted dozens of times a day through phone, email, linkedin, etc. So be prepared. Do your research. Customize and personalize your outreach. Try to be different.

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

Howard: I work with Sandler Sales Management. Jim Mattei is an incredible coach.

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

Howard: One of the best sales books I have read is Mahan Khalsha "Helping Clients Succeed"

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

Howard: Inc Magazine and Harvard Business Review

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

Howard: Be the first one in and the last one to leave...

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

Howard: I think sales technology has evolved quite a bit over the years in terms of prospect intel, automation, forecasting, etc. It will be interesting to see how this technology continues to evolve and what new or different skills the sales professional will need to be successful.

Sales Assembly: How has your approach to sales changed over the years?

Howard: A much bigger focus on process and qualification. More emphasis on identifying and removing roadblocks. Much more willingness to walk away when the investment of time will not yield the best return. To do so you must get on equal footing with clients (as Sandler calls this "parent parent") and make sure you are constantly driving the process and not letting the process drive you.


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