Alan McKinnon has sailed from state politics to enterprise software, navigating the nuance required to excel in both arenas. Today he serves as the Revenue Program Manager at Boston based startup Jellyfish, a rapidly growing enterprise software company helping engineering teams work smarter.
Alan is from the North Shore. The oldest son, he is the third Alan in the McKinnon line because his dad “always wanted a name he could remember”. The MacKinnon’s have Scottish roots but dropped the “a” on the ride over, thinking a more Irish sounding name might help them assimilate faster in the Boston area.
Both of Alan’s parents have been critical role models throughout his life. They each have MBAs and are entrepreneurs at heart. Alan’s mom ran a jewelry business after graduating from Harvard Business School before becoming an executive coach and teacher at HBS for many years. Alan’s dad got his MBA at Babson and has held a variety of executive finance roles in the semiconductor industry, frequently traveling across Asia and North America, and fueling his love for travel.
Growing up near the water, Alan and his entire family were big sailors. His younger brother plans to join the industry, training in a composites technology program down in Rhode Island and Alan sailed competitively while completing his undergraduate Political Science & Economics studies at UVM.
After graduation, Alan joined Charlie Baker’s re-election campaign for governor. Alan ran the field office in Baker’s home town of Swampscott. He coordinated local events, helped fundraise, knocked on doors, and made calls to get out the vote before the primary season. After staying on to help with the re-inauguration, he landed at the Department of Housing and Community Development.
In a technically focused role, he worked with developers to build out an online application for public housing across Massachusetts. Alan helped turn legislation into a properly functioning website that complied with local law. As a part of a small taskforce of project leaders & developers, they helped launch a new and improved application available in 10 different languages covering 240+ housing authorities across the state.
Alan learned a ton about state level politics and the machine that runs in the background from polling data to campaign operations to cross functional coordination across a vast network of people and relationships. He learned about the extreme nuance and complex positioning in politics. In a way, he helped stand up an MVP and run a massive campaign to market that B2C product via guerilla marketing. Pretty good startup experience.
After 6 months working for the Commonwealth, Alan began to think about what was next. He wanted to step outside of government and try the private sector. A close college friend of Alan’s had moved out to Southern California to take a role at finance technology company Blackline and put him in touch with their Business Development team.
Blackline is a publicly traded vertical SaaS company that helps accounting & finance teams automate their workflows. He flew out to Los Angeles for the interview and arrived at their offices…in a suit. They were probably wondering if they themselves were being audited. Alan came prepared to pitch them on their product without any accounting knowledge, dressed as an accountant, and landed the role! In less than two months he uprooted his life with just a couple bags to move out to Tinseltown.
Blackline was a scaled GTM organization with 100+ BDRs globally and established infrastructure as a public company. The team put him through a formal, month long training program before he hit the phones. Alan looks back at that training program as a foundational piece of his later success in Sales.
When Covid hit and the BDR team at Blackline went remote for the first time, Alan drove back across the country for a month visiting national parks (between meetings) and working his way back to the Boston area to live with some friends.
He was ready to make an outsized impact at an earlier stage company as an early BDR hire. Prospecting a targeted list of Boston area venture backed B2B SaaS startups, including Accel backed Jellyfish, he sent a note to “hello@jellyfish.co” with his resume. And he actually got a response, no suit required! Jellyfish’s VP of Sales, Ben Solari, just happened to be recruiting a new BDR class. Alan even interviewed with co-founders Andrew Lau & Phil Braden who helped interview Jellyfish’s first 150 employees.
Alan was hired as the 5th BDR in the initial class. He was impressed by the caliber of the team, product, and potential of the platform they were building. The company’s growth was rapidly accelerating with distributed work as a tailwind. For remote R&D organizations with hundreds of engineers, Jellyfish is a “flashlight in the darkness”. The company had a perfect product for the moment amid the shift to remote engineering workforces.
Since Alan came from a much larger Sales organization, he was able to work backwards to help build out more efficient handoff processes for their Sales team to help grow the initial customer base. As Jellyfish raised their Series B & Series C rounds of financing, the company was hiring 1-2 BDRs a month for a full year.
Alan would help onboard the new reps, get them trained up, and 3 weeks later get to work hiring another cohort. He helped build out the new hire training process for the Business Development team, authoring their initial management process from scratch while hiring a talented group. He was promoted to Team Lead, getting a crash course as a player-coach to more than 10 reps, and learning that successful BDRs come from a variety of backgrounds and skillsets.
As Alan got more exposure to other parts of the company, working closely with Marketing and Sales leadership, he was promoted to Business Development Manager. Alan really loved working with the management team and the other talented leaders at Jellyfish. Then, for the third time in his Jellyfish journey, he got to author his next job rec, stepping into the Revenue Programs Manager role.
Today, he helps manage Revenue programs without a natural home across Jellyfish’s GTM operations. His responsibilities include getting the most out of their software tooling, revenue enablement programs, and building out TAM (total addressable market) analysis alongside Jellyfish’s CFO to help right size their market assumptions. Alan also recently took on a project with a web development agency, in a callback to his Department of Housing days, where he managed the launch of the new Jellyfish website in under 90 days.
One of his favorite responsibilities is working with Jellyfish’s CEO, Andrew Lau, on executive engagements. He helps nurture existing high value pipeline opportunities with curated notes & content from Andrew to help add a white-glove approach to strategic deals.
If you want to work at a growth stage company in the Boston area, Alan thinks Jellyfish has one of the best market potentials with an awesome group of talented people. An exciting business with its best days ahead.
See the Future to S(c)ail the Middle
Alan knows firsthand that building a team from scratch takes a leader’s full involvement of time and energy where you have to be on call…almost always. Most Revenue leaders know the responsibility of managing a team of 10+ BDRs – hiring, backfilling, promoting, and establishing process. Managing an entry level team requires knowing that they all want to grow in different ways, so keeping them motivated and performing at a high level month after month is a critical responsibility.
When Alan began scaling the team, he was lucky to have already seen the future at Blackline. With their mature infrastructure, he could outline a course he needed to chart at Jellyfish. The present was pretty clear, it was the murky middle he needed to navigate.
Alan dove in. He used HubSpot blogs, built spreadsheets and dashboards, and tapped into peer groups to help manage his team’s time and resources. He leveraged internal and external recruiters to fill roles. He built a consistent 30/60/90 day ramp plan for every BDR that came onboard tailored to their experience. It covered “startup basics”, “where are we as a company & team”, and the financial metrics their team tracked monthly.
Software engineering was a big learning curve for most of the team too. Jellyfish’s BDRs are required to talk to engineering leaders all day so the onboarding needed to be technical enough to teach reps how to do their job, understand the industry, and why prospects should care about Jellyfish’s product.
Alan built a structure but also carved out flexibility to deal with each of his team members individually. Some reps are good cold callers, some are better on LinkedIn, and some are great e-mail sequencers. Metrics may vary and are not always correlated to meetings booked. He’s learned to give the team the freedom to experiment in order to drive results.
On the personal side, he found balance by planning dedicated time off where he could fully unplug and look forward to spending time in a new place. He’s built a strong network outside of work to help him stay balanced. By prioritizing the most important things well, he’s been able to stay energized and work toward established goals more clearly.
3 Career Insights / Learnings
Know Your Manager – “Having a successful relationship with my manager is so important. Whenever I join a new team or company, I work hard to build a successful relationship with my manager as that person is often the launchpad for upward mobility. Having seen both sides of the equation, I try to be cognizant of putting myself in the best situation possible”
Balancing Life & Work – “I used to live to work. Hard work is necessary to move up in your career but you also can’t forget that you’re there to learn new things, experiment, and explore what you like & don’t like as that informs what you want to do later in life. Paychecks aside, what do you enjoy doing outside of work? Who do I want to be as a person outside of work? It took me some time to sort that out.”
Invest Long Term – “Joining a company is an investment that requires time to pay off. As I enter the prime part of my career, I know that my time at Jellyfish has given me the opportunity to learn more about company building, software, management, and other aspects of the job that I could only experience first hand. I’m embracing every opportunity to learn as much as possible to make the most of my investment”
Alan has loved the different opportunities he’s received at Jellyfish, learning how to help run a high growth venture backed company. One day he might like to start his own. At the very least, Jellyfish is helping him build a skillset for future opportunities as they come. He enjoys putting the pieces together to make a growing company run more smoothly.
Outside of work, he’s busy building his network in Boston and always looking to meet new people around the startup ecosystem. If you want to learn more about Alan you can find him sailing around New England in the summer, skiing in the winter, or helping build out a GTM powerhouse at Jellyfish. And of course on LinkedIn too. Thanks for sharing Alan. Jellyfish’s new website looks great and we’re excited to see all the Revenue programs you help develop in the quarters ahead!