Julia CampbellBranded Content Project Manager

The local business community needs your help. In fact, they need your help more than ever.

Small shops, local restaurants, community organizations and hometown service providers are looking to you as their communication guide to help them reach their customers … reach your audience.

It’s a tough job on a good day, but even tougher when you can’t bring people together in one room to share ideas, talk strategy, or communicate a message.

So it’s time to go to the screen – big screens and small screens – to virtually connect with the business community. In the coming weeks, we’ll share examples from three media organizations that are not just connecting in creative ways, but succeeding in bringing together their business communities with a little ingenuity and a little internet.

We’re starting our series with Masthead Maine.


The transition from live to virtual events is proving to be successful for the team at Masthead Maine, so they didn’t stop at one series, but launched three.

“Like a Boss Now”, “Making it Work” and “Maine Live” are unique series focused on highlighting businesses and the community in Maine.

“Like a Boss Now” is a virtual interview series that has roots as an in-person event. The Goal: to attract high-level B2B audience that would also be attractive to sponsors. The Format: one-on-one interviews between Masthead Maine’s CEO Lisa DeSisto and top Maine CEOs.

We talked to the team in Maine on a recent Branded Content Project group call about their strategy, success, and future plans.

Kate Simmons Tillotson, director of strategic partnerships for Masthead Maine, explained the series.

“We originally had a live event called, “Like a Boss” where our CEO interviewed other top Maine CEOs. Our number one goal from our sponsors and our prospects was they wanted to meet other decision makers in business. The people in a company that would make decisions about the banker, the insurer, the benefits broker, the accountant, and who to use for those outside services. Typically in Maine, in small shops, the CEO or the CFO is making those decisions. We wanted to create content that would attract the top of the food chain. We had the top of the food chain talk to the top of the food chain.

“Enter March, and we wanted to shift our live event strategy and so together our team of four decided with our CEO to shift, of course, to the webinar. We also realized that people were really planning for the now, and I think that instead of planning six weeks out to attend something or even two weeks, they are planning more like twelve hours or twenty-four hours. So, we took advantage of that change in mindset and scheduled seven “Like a Boss” interviews once every Friday at 1:00 p.m. for seven weeks.”

Tillotson continues, “As we all know, the really fun thing about webinars is that you do not have to travel to a particular place to experience it. You can do it from anywhere. This enabled us to start to engage our other media properties that we worked with, engage their lists, and secure people from all over the state.

“Actually, we started using our Branded Content Project grant money to start to secure an audience from all over the country. The digital audience is about twice the size of our typical audience and we’ve also increased our email list size by using native ads and Facebook to drive more traffic to our content and drive more sign-ups.

“I will say that what is super interesting to me now is that we really took advantage of the immediacy of people’s mindsets and wanting to hear about leadership now, and how people were immediately pivoting. For instance, how L.L.Bean was using the materials that they need to use for dog beds to make masks, and how Stonewall Kitchen changed their production, so that people could still be safe in their manufacturing environment.

“I think that mindsets are shifting now, people are able to do more planning looking ahead. I think that our webinar promotion strategy and content and strategy will change a bit as well to reflect that more positive outlook, which is really exciting. I will also say, we are able to secure and keep our live event sponsors, and keep that revenue. Then for two presenting sponsors, we’re able to bump them up to a higher investment for these seven webinars. The single most important thing that one of our sponsors cares about is the email list of the attendees. That goes to their producers. It is their lead generator. The beautiful thing about webinars is that when they are free, you know that you are probably sharing your email address with sponsors and we make that clear in the sign-up. And then we leverage every point of contact to get that sponsor logo in front of our audience. We also allow our sponsors to speak at the beginning of each webinar.”


The team in Maine also sees this as an opportunity to nurture relationships.

“I think we all love to think about, what are the other benefits beyond engaging readers and driving subscription revenue? But how are you engaging more relationships? How are you opening doors? How are you lifting all those?” Tillotson said.

The second event series they adapted was Business Breakfast Forums, morning events for a B2B audience where they take a trend in business and people who are solving for that trend. The Masthead team gave it a little bit of a refresh in these times to reflect how people are changing their business models to address the current environment and called it, “Making it Work.”

“We have had a lot of discussions and two live events now with restaurant owners, distillers, concierge services for those experiences. We are all small teams; how do you get the most done as quickly as possible? It is relatively easier to set up a CEO in an interview because he or she has a support team. It is much harder to be lining up small business owners who are in the thick of their business who might not have a headshot, who definitely do not have a bio and who definitely do not have a scheduler. So, just from a nitty-gritty logistics perspective, when you are a small team, the CEO-to-CEO thing is pretty streamlined, but when you get more into the weeds with other folks, the work definitely increases almost exponentially, but well worth it,” Tillotson said.

“We have increased our email list by about 10% and are seeing roughly equal, if not, more attendance on these webinars. The thing that we are seeing, is that we are getting more prominent people within the community and more business owners on the webinar because the time is different and it is more accessible.

“So, in our market, quality versus quantity is definitely part of the conversation. We are seeing higher quality with Making it Work, not to say that our Business Breakfast list was low quality, but we are definitely seeing a higher level of decision-maker with the webinar format, which is really exciting. We are looking to evolve that into different sectors,” said Tillotson.

Molly Adams, content specialist for Masthead Maine, shares details on their third event series, Maine Voices Live.

“Our third event that we took online is a marquee live event,” she said. “One of the first events that we launched in 2016 was called ‘Maine Voices Live.’ They are on-stage interviews with notable people from Maine and staff members from the Portland Press Herald or our sister publications. Bill Nemitz is an extremely popular columnist for the newspaper. Joseph Owen was a longtime editor at the Central Maine papers, and they are going to be talking about Maine’s bicentennial. We have been doing a number of history features.”

Adams also explained that securing great guests in the past had been a challenge due to travel budgets as timing.

“So, these webinars have given us great access to people. We have Timothy Simons, who starred as Jonah Ryan on Veep, and we’ll have astronaut Jessica Meir, who just came back from six months on the International Space Station and did the historic all-women spacewalk while she was there,” Adams said.

We asked the team if these events will continue as virtual past COVID-19. Tillotson believes they will.

“I think people really enjoy the one-on-one interaction and certainly, that is really powerful in the business community. I do not know how comfortable people are going to be in a room with a hundred and fifty people and will probably have to wait a very long time for that scenario to be possible. Even when we do return to that, I think webinars are here to stay because you have removed so many barriers to participation, and that’s what’s really exciting. From a logistics standpoint, there’s no name tags. There’s no donuts. There’s no banners to schlep around. So that is nice, right? I think it is going to be a mix going forward and that way you can reach the most people possible to experience the content, which is really the driver for everything.”