• August 19, 2015

Legendary Salespeople: Matthew Flanagan

You know the saying that when you need something done, to ask the busiest person you know? You get the feeling that if you need something done, you could ask Matthew Flanagan of SessionM. When someone works in enterprise sales, you know they have a pretty busy schedule already – pile on the crazy hobbies like surfing and craft home brewing, you have to know that these legendary salespeople are on top of their game.

Not many people know start-ups like Matt. He has a particular nose for companies that are just starting to grow their sales teams post Series A  – and has the track record to prove it. After stints at DoubleClick (acquired by Google) and BuddyMedia (acquired by Salesforce), Matt is currently at SessionM. SessionM offers a unique platform for driving loyalty marketing on mobile apps, specifically in the enterprise space.

Since Matt is a sales ninja that seemingly can get a lot of stuff done very effectively, I had to ask him how he keeps it all together. He was nice enough to talk through some of his tips for sales success, as well as some tools he uses as part of his workflow.

Tips For Success

To quote Kenny Rogers – you gotta know when to hold em and when to fold em.

Matt: Understand that your time is very valuable, so be hyper critical of where you allocate it. Especially when you’re at a startup, time is an extremely precious resource. Don’t chase deals that are probably going nowhere. And if you are hunting a whale – bring a big spear.

Polite Persistence

Matt: There’s a fine balance between be annoying and being politely persistent – find what works for you. I’ve found that it can take up to 6-7 polite outreaches to get someone on the phone and engaged. Understand when you actually have someone’s attention, and when it is somewhere else

Get used to hearing “No”

Matt: It can take a lot of ‘No’s’ before you hear a yes, especially when dealing with a complex sale. At bigger companies, there are many people involved with the decision making process – so don’t take the first no you hear as a total rejection.  Only a small percentage of people are unphased by the fear of rejection – become one of those people.

Tools Of The Trade

YesWare

Matt: The efficiency of tracking and seeing the click throughs on the links are huge.

Clearside

Matt: An app that allows for presentations via the web. It’s browser based and integrates with Salesforce. It also handles SF lead creation from forms beautifully.”

Spiro

Matt: It gives me a mobile view into my deals that is intuitive and easy to use. I can edit opportunities with a few taps and easily log calls on the go.

Hubspot Lead Management

Matt: Any solution for lead scoring that can help keep me focused on the leads I actually care about.

Photo by Skyler Smith