Expanding Intelligent.ly's Tribe

I couldn’t be happier to have joined the Intelligent.ly team to develop relationships with our current and future partners. Having spent nearly a decade in high-growth, Boston-based startups, I have worked in industries ranging from retail to enterprise software. As a founding member and former Director of Blank Label’s Retail program (Best of Boston 2014, 2015 and 2016), I focused on building teams and service standards in pursuit of a differentiated approach to retail. Growing the company from an e-commerce business to three brick and mortar locations in under two years was a big win. Most recently, I expanded EverTrue’s customer base in the Southeast and soaked up the energy of a rapidly growing SaaS company. I’ve been fortunate throughout my career to work with incredibly talented teams (many of whom are part of Intelligent.ly’s tribe) in hitting some very lofty goals.


I say tribe, because in just a few short days on board, I’ve experienced Intelligent.ly’s ability to create an environment focused on fostering human connection. We are a community of like-minded people, working together, contributing individual talents in pursuit of a greater, common goal. Moreover, Intelligent.ly’s tribe extends beyond our small and mighty team. We have the unique opportunity to work alongside Boston’s brightest companies, developing their future leaders, scaling their impact and creating a premier community in a thriving start-up scene.


Of all the learnings, I’ll never forget my first leadership training. The opportunity to stretch in a safe space shifted my mindset from doing to developingThe result was a new generation of internal leaders. They allowed me to walk away when the time was right, knowing that my role was transitioning to the most capable and committed hands. In two years time, the fresh-out-of-college hires grew quickly enough to earn a seat at the table. How rewarding is that?! The experience was an inflection point in my career that put me on the path to joining Intelligent.ly.


Already I’ve felt the energy and momentum from our EMERGE and Exchange participants. I’ve heard from partners about the ripple effects of investing in their talent, and I’ve listened to the stories of personal growth from alumni. These anecdotes are just the tip of the iceberg.

So here’s my ask to both current and future members of the Intelligent.ly Tribe: please reach out to connect.  My calendar is open and I’m anxious to hear your thoughts on how we can continue to make an impact on Boston’s future generation of talent!

A Season of Change for Intelligent.ly

It’s been pretty incredible to watch the transformation of Intelligent.ly over the last four years. We started by connecting people through skill classes, and grew into developing Boston’s next generation of leaders. Our vision has expanded and our reach has grown, and now it’s time to usher in a new chapter.

This week, we say goodbye to Abbie Weeks, who has been an incredible leader for the Intelligent.ly team over the last two years. Our mission is one that supports the personal growth and development of leaders, and Abbie is ready to kick off a fresh chapter in her own career. We couldn’t be more grateful for the passion and energy she has brought to Intelligent.ly, and we’re cheering for Abbie as she transitions into her next gig. From the very first day she entered our world, she has brought laughter, positivity, and a relentless drive to our business that has helped us grow our footprint, impacting over 75 startups across Boston. Her commitment to creating exceptional experiences has elevated our programming, touching hundreds of leaders’ lives. Thank you, Abbie, for everything. We’ll miss you.

We’re so fortunate to have another leader in our midst who is stepping up to lead Intelligent.ly through our next stage of growth. Gabriela McManus has been with the Intelligent.ly team for the last year as our Director of Learning and Development, and will now move into the Executive Director role. Gabriela joined us from Infusionsoft last Summer, and dove right in to begin facilitating our leadership programs and improving our curriculum. She has deep personal knowledge of what it’s like to live through the highs and lows of a high-growth startup, we’ve been blown away by the fire and insight that she brings to our team. Learn more about Gabriela’s vision for Intelligent.ly here.

We doubled our impact over the last year, and I can only imagine what’s ahead with Gabriela at the helm. I’ve never been so excited about our future; every company in our community can benefit from the power of investing in our leaders, and we’ve only scratched the surface on what’s possible. Connect with us here to follow along with our journey or learn more about our programs. Thanks for all the support you’ve shown to our team over the years. We’re grateful to be part of this community!

A Vision for the Future

Our vision is simple - we’re building a community of leaders. The operative word being community.

Through a career focused on management and leadership development in rapid-growth companies, I have seen firsthand the tremendous impact of intentionally building individual and organizational leadership capacity. When I heard about Intelligent.ly’s work supporting rapidly scaling startups committed to growing and retaining talent, I knew I had found my place.  

In the year that I have been here, we-fine tuned our Exchange program for new managers, launched EMERGE for individual contributors and kicked off two new company workshop offerings. These have expanded our footprint and doubled our impact.  The stories that come out of these experiences are what I am most proud of - the anecdotes of small behavioral changes that led to big results, the shift in mindset, the relationships that are forged - this is where the impact is happening. The ripple effect is massive, but this is only the beginning.

I’m tired of Boston’s tech community being perceived as San Francisco’s lesser East Coast counterpart. We have a tremendous amount of talent, a rich ecosystem of universities, and access to capital in our own backyard. Intentionally developing our next generation will only serve to increase our advantage. We’re fueling this growth at Intelligent.ly in our leadership development programs, and building a new normal for leadership across our city that centers on a hands-on, collaborative approach.

How we’ve shaped our programs is an output of who we are as a team - catalysts for connection, startup-focused entrepreneurs, and trusted experts. We’re rethinking leadership development based on our own experiences growing companies, by blending research-based methodology with a hyper-growth perspective. It isn’t good enough to know something; you have to know when and how to put it into action.

Coming from startup roots ourselves, we understand and embrace agility, and produce an environment that inspires innovation. We encourage everyone who passes through our programs to focus less on the answers, instead, asking the right questions to challenge the status quo and be a disruptive force.  

Over the next few years, we will focus on one thing: becoming the standard for leadership development in Boston. By partnering with rapidly scaling companies, we will make it easier for entrepreneurs and startups to focus on their work and their purpose, because they know we have them covered when it comes to developing their people.  

In a city where we have some of the best educational institutions in the world, Intelligent.ly provides a different solution - one that complements our historic ties to education and helps propel us into the future. At one of our Exchange programs last year a manager approached me to say he wants an Intelligent.ly sweatshirt showcasing his non-traditional MBA. I envision a dense web of alumni of our ‘non-traditional MBA program’ coming together to make our community even stronger over the next decade. This is our vision for the future--game-changers making an impact on our city, connected by their Intelligent.ly experience.

3 Things You Can Do When You Don’t Have Time for Coaching

This post first appeared on BostInno.

“When we started our company, we were scrappy and lean. We hired a bunch of people in their early 20s with tons of hustle. Now we’re growing like crazy, and they’re in over their heads. It’s really not their fault – they’ve taken on more responsibility, we want to help them grow, but no one has the time for coaching.”

I can’t tell you how many times I’ve had this conversation with startups.

We invest so much time and energy in staying ahead of the market by developing new product features. Yet over and over again, we lag in developing our people. We wait until the pain is acute, when attrition skyrockets and people start leaving for better opportunities, or employee engagement and happiness hit rock bottom. Remember who builds those product features – people.

One thing’s for sure: employees often feel the pain before their leaders do. A Deloitte study of millennials noted that among employees who are likely to leave their employers within the next two years, 71 percent are unhappy with how their leadership skills are being developed. SHRM reports that the direct replacement costs of employee turnover can run as high as 50% – 60% of an employee’s annual salary, with total costs ranging from 90% to 200% of annual salary. That’s a whole lotta Benjamins.

When the reality finally hits us in the face like a bucket of cold ice water, managers get all the love. We double-down on sending managers to workshops and conferences and investing in coaches – but what about individual contributors? Plenty of employees deliberately choose an individual contributor path (HubSpot’s Pamela Vaughan wrote agreat article about this). Others are high performers on the road to future management roles. They’re not managers, but they are leaders. And they’re critical to a company’s success.

Boston startups are starting to take note. Companies and programs like Intelligent.ly EMERGE are stepping up to shine a light on the importance of developing our city’s next-generation of leaders. I’m a co-founder of Intelligent.ly; at the last Emerge event, I heard from a handful of Boston’s best tech recruiters and leaders.

HubSpot’s Katie Burke shared her perspective: “One of the most critical steps in retaining top talent in Boston is ensuring that rising stars in the tech community receive the training, support and network they need to grow personally and professionally in their careers.” They’re not alone.

Loren Boyce, Director of Talent at Yesware echoed the focus on investing in personal development for individual contributors, “We are all-in when it comes to providing resources and experiences that help our employees reach their professional potential.”

What can you and your company do to develop these leaders? Here are three tips:

Start a Conversation

The first step to developing individual contributors is understanding how they want to grow. Let your team members know that you want to support their personal development. Set up a 1:1 to talk through their personal goals, and together, consider the resources you can help provide. This might mean connecting them with mentorship opportunities or investing in skills training. You won’t know until you ask.


Experts go back and forth on the science and applicability of the various personality tests that dominate leadership development conversations. My perspective is that if they help you better understand something about yourself – your strengths, and the way you operate – it’s a win for everyone. 16Personalities provides a simple and free personality test based on the Myer-Briggs approach. Encourage your team members to learn from the insight that resonates for them…and don’t stress about the areas that don’t.

Organize a Leadership Lunch & Learn

Consider how many individual contributors you could reach with solid leadership advice if you leveraged your internal team to set up a weekly or monthly Leadership Lunch & Learn. Invite respected leaders from inside your company to share leadership advice and tips that helped them through their own careers.

Close your eyes. Think about all the individual contributors in your company. Consider what you could achieve if they truly had the coaching they need to fulfill their leadership potential. Now envision them walking out the door because you don’t have time to support them. Scary, right?

    It’s Not Easy Being Green: A Millennial’s Guide to Leadership

    Big news, guys. This month marked my first ever work anniversary. There was blood, sweat, and more tears than I’d care to admit, but here I am, one year after signing onto my role as Intelligent.ly’s Content & Community Specialist. For most seasoned professionals, this is no magnificent feat, but my fellow Millennials (and Kermit the Frog) know that it’s not easy being green.

    If television has taught me anything, it’s that most 23-year old Communication Studies majors are doomed for years of frustration and debt before having a job they love. I was one of the lucky ones, I guess. In hindsight, before joining Intelligent.ly, I was naive to the monumental importance of leadership. The simple truth is leadership can’t be taught in college; it’s learned from experience – and many of us don’t get direct access to learn from strong leaders early on in our careers.

    After 31 Exchange sessions, 2 EMERGE workshops, and an endless supply of leadership inspiration from the Boston community, I’m by no means a guru. But I havelearned a thing or two about what makes organizations and teams successful from 500 people across 50 startups:

    Know yourself: This is Day 1 of Exchange, and it’s critical for us youngsters. In a sea of resumes, self-awareness can be the thing that sets you apart from the pack (Whitney Johnson calls this the “competitive advantage”). Knowing your strengths and your weaknesses will allow you to find areas you can really shine, and generate baselines for meaningful growth. It also helps to know how you like to be communicated with, and what truly motivates you.

    And, know your team: We spend so much time working that our teams become like our families. To keep frustrations low and productivity high, it’s important to know what each member loves, makes them tick, and how they learn best. So many lapses in productivity are caused by miscommunication. Ask each member what they need from you, in terms of communication. You can use this blueprint to share each other’s quirks!

    Conflict is good: Startup life can be emotionally taxing, and conflict is inevitable. Create an open environment with your team by being vulnerable, sharing your challenges, and consequently creating trust to ensure healthy conflict. This means everyone’s perspective is valued and team members are open to growth.

    Ask for help: Spoiler alert: at 23, I still don’t have all the answers. And that’s okay. No one expects you to. Give yourself a break, and lean on others for advice and best practices. Our program, participants and guest speakers alike talk about the importance of having a meaningful network. At Exchange, we have participating managers ask their peers for advice. Create your own web of trusted individuals you can ask for help, and learn from them.

    Lack of experience ≠ lack of leadership: This one was an eye-opener for me. I spent months diminishing my own opinions, firmly believing that those with more experience knew better. I’m still working on it, but I’m slowly learning that you can be a leader…even if you were born in the ‘90s. You were hired for a reason, and your opinionmatters, if nothing else to provide a new perspective.

    Create your own path: What I love about my role at Intelligent.ly is that it’s not set in stone. I’m young; I don’t know what I want yet. I have no 5-year plan. And startups are the perfect place for that. My role (and yours) can become whatever you want it to be, if you prove you’re worthy of the reward.

    Whitney Johnson’s Secrets to Disrupting Your Career

    When you find something that works, it’s easy to get stuck in a rut. But the most successful startups aren’t the ones that find a recipe for success and stick with it–they’re the ones that constantly aspire for more, iterating and innovating in powerful new directions that leverage their core capabilities to disrupt stale models.

    According to Johnson, personal disruption is “the act of using a practice employed by companies—wherein a product deemed inferior by the market leader eventually upends the industry—and applying it to you as an individual.” Her concept of disruptive innovation is rooted in the S-curve (see image below), with three distinct parts: competence (gaining your footing), confidence (thriving), and mastery (comfort).

    The S-curve of disruptive innovation

    The S-curve of disruptive innovation


    The S-curve of disruptive innovation

    Disruption is Whitney Johnson’s bread and butter. As an Author, Speaker, Advisor, and one of the 50 Top Management Thinkers of the World, she knows what it takes to harness the power of disruptive innovation to make amazing things happen. In November, Johnson joined us for Intelligent.ly EMERGE, a one-day leadership workshop designed to help individual contributors become effective influencers, for a powerful keynote about investing in continuous innovation.

    We caught up with Johnson to tap into her knowledge about how to stay fresh:

    You’ve said that when things become easy and you’re not feeling challenged or learning new things, it’s time to jump to a new curve. Do you have advice on how to know WHAT to jump to?

    Analyze how what you do well maps to what others want done by answering:

    1. Are there stakeholders whose needs are not being met? What are they?
    2. Are there a lot of people trying meet those needs (e.g. 50 people applying for a job), or has there ever been a job posting (e.g you’d create a job) for a need that isn’t being met?
    3. Does this need you want to meet leverage your distinctiveness (what you do remarkably, uniquely well)? As in, it’s so easy for you, you don’t value it because it’s as natural as breathing?

    The whole point of disruption is to move up the y-axis of success over the x-axis of time. When you disrupt yourself you are making the conscious decision to move down the y-axis, on the premise that the slope of your next curve will be even steeper, leading to another period of rapid growth.

    Jumping from secretary to investment banker to analyst to investor had to have been daunting. How did you channel fear to help you grow vs. letting it become a constraint?

    It’s pretty easy to talk about this after the fact. So, what I’m about to say makes these moves sound much tidier than they were. That said––A constraint simply defined is something that you bump up against, and in bumping, you get information. Like a skateboarder. They learn quickly because they receive fast and useful feedback. Fear is typically characterized as a foe, but it’s also a friend. Follow your fear and you’ll know what matters to you. In this way, rather than a check on your progress, it becomes a tool of creating you.

    Regarding pursuing market risks (vs. competitive risks) – is this possible to do inside an established company? How can individuals pioneer a new idea effectively?

    Even inside of a large company there are ideas people haven’t had and projects people don’t want to take on. These are opportunities for taking on market risk. Think about Intuit’s Fasal. When they wanted to make a difference in India there were lots of routes Intuit could have taken. Instead they sent three engineers to rural India for three weeks and said figure something out.

    One day during a torrential downpour that found themselves at a bus stop with local farmers. As they chatted they discovered the farmers didn’t have access to commodity prices. Having found a problem to solve, they could have now thrown a lot of money at it. But they didn’t. They just started manually texting price and buyer information, iterating their way to a solution. Notice how this process was so low-cost, so low-risk, so where -no-one -else-was-playing, the odds of it getting quashed, were practically zero.

    Because Intuit encouraged its people to play where no one else was, which also included very few resources––until they knew they had something that worked––today there is a service known as Fasal, a sophisticated text-messaged based platform, helping farmers get the best price. Over 2 million users who enjoy more than 20% increase in their bottom line.

    Boston has an “Innovation District,” and is increasingly becoming known as a leading city for innovation. Do you think the word “innovation” is becoming overused? What do you want people to understand about the meaning at its root?

    In my experience, when someone uses the word innovation, they are signaling they want to try something new. Wanting to improve, to do better and be better, is always good. Always. Where I think we get tripped up is when you and I attach different meanings to this word.

    My definition? Innovation is about moving from stuck to unstuck. There are lots of ways to do that. The frameworks of disruption are one. Which is why I wrote Disrupt Yourself. I wanted to convey that companies don’t disrupt, people do. Here’s how. In 7 steps. My hope is this: That I have made a strong enough case around the ‘how’ that we can move forward together on the ‘do’.

    Ready to invest in developing innovative leaders inside your company? Enroll in the next Intelligent.ly EMERGE workshop.

    10 Secrets to Great Leadership from Diane Hessan

    After recently leaving her 13-year gig as Communispace CEO, Diane Hessan stepped into a new role as CEO of Startup Institute, a Boston-based company dedicated to helping people transform their careers and find jobs they love. There are few CEOs as charismatic and candid as Diane, so it’s no surprise that she is a stellar leader, committed to developing top talent in Boston’s startup community.

    Last Tuesday night, Diane joined Intelligent.ly’s Abbie Waite for a fireside chat about leadership with 125+ members of our community. The audience was astounded by Diane’s openness—it was like chatting with an old friend about how she casually became CEO of an international organization. In spite of immense success, Diane maintains her humility, paying forward the wisdom she’s gathered over her remarkable career. Here are her top 10 secrets to great leadership:

    1. Build your A-Team: From Diane’s experience, “A-players” transform teams and help take them to the next level. Diane supports her team by spendinghours interviewing key players to ensure they’re a “fit,” build rapport, and learn what matters to them.

    2. Being honest ≄ being mean: Leadership is about being direct and objective. Sometimes you need to have difficult conversations for the good of the company, but it doesn’t have to be mean. People value the truth, especially when it helps them in the long run.

    3. There’s no such thing as, “I’m not a leader yet:” You can be a leader at any level. Leadership is more about empowering others to lead than getting them to follow.

    4. Serendipity: Most of your life is the product of a few “aha” moments. Diane keeps these tucked away and remembered, and they shape how she leads her team.

    5. Listen more than you speak: For her first month at Startup Institute, Diane did almost nothing but listen. She asked each team in the organization about their unique challenges, then began to formulate solutions.

    6. You can’t do it all: You may be a leader, but that doesn’t mean you can doeverything well. Instead, choose a few things you can do really well to impact your team, and focus on that!

    7. Don’t keep secrets: Diane believes in being open and transparent with her team. Two weeks into her new CEO position, she laid out all the numbers for her team, a shocking and unprecedented move. This small action went a long way in helping her team understand how they contribute, building trust, and reducing anxiety.

    8. Keep the conversation going: Leadership is all about having a continued conversation, and you never stop trying to raise the bar. Ask your team, “if you could wave a magic wand, what would this team be doing?” and get everyone involved in the vision.

    9. You’re leading PEOPLE: Well, duh. But we truly can’t overstate this enough. Everyone’s different, and human beings want to know that they matter and that you’re thinking of them. They need to know what the team vision is and that it’s okay to screw up sometimes.

    10. Embrace question marks: In rapidly growing organizations, scaling leadership is just as important as scaling the company itself. This oftentimes means not knowing all the answers, but rather having a diverse team who you can trust to have the answers you don’t have.

    Want more great leadership pointers like these? Attend our next Leadership + Libations event OR learn more about Intelligent.ly Exchange!