Lashea Webb of Job Opportunities Task Force (JOTF): “BE BRAVE”

BE BRAVE: You cannot lead and make impact without Being Brave. You will miss 100% of the shots you don’t take. So, don’t be afraid to take risks. Great success is the product of learning from failures and setbacks. Challenge convention and act with conviction. I grew up in foster care and my mentor and […]

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BE BRAVE: You cannot lead and make impact without Being Brave. You will miss 100% of the shots you don’t take. So, don’t be afraid to take risks. Great success is the product of learning from failures and setbacks. Challenge convention and act with conviction. I grew up in foster care and my mentor and social worker, Jodie Bloom, asked me to speak on behalf of my group home at a meeting with community neighbors who wanted to see our home closed.

As part of my series about young people who are making an important social impact, I had the pleasure of interviewing Lashea Webb.

Empathetic and visionary activist and advocate Lashea Webb is creating a future grounded in economic mobility, security and equity for all. At just 28, this Baltimore-based, Jamaican American woman is the program manager for the Job Opportunities Task Force (JOTF), a nationally renowned non-profit that is celebrating its 25th anniversary in 2021.

She has helped make JOTF into a national-paradigm in workforce development (job training and creation) and criminal justice reform. JOTF exists to eliminate education and employment barriers for low income and marginalized populations, especially Black and Brown communities, by transforming the systems that create and perpetuate those barriers.

Lashea shares with us how a childhood spent between Jamaica and America, living in the foster care system and her father’s interaction with the criminal justice system inspire her changemaking.

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit. Can you tell us a bit about how you grew up?

I was born in Brooklyn, New York to first-generation Jamaican immigrants. My parents saw America as a beacon of hope and opportunity and came here committed to providing a better life for their family.

My father, Alvin McClean, came to the United States first. My mom, Suzan Webb, would follow him to Brooklyn. Their life and plans were abruptly upended when my father was incarcerated during his first year in the country. My dad is an influential and profound part of my life, yet he has been incarcerated since my birth. To this day, we talk twice a week.

I was raised between Brooklyn and Jamaica, largely by a single mother. My mom was fiercely proud of our Jamaican heritage. She loved to cook and ensured we ate fresh vegetables and fruits. I acquired an enduring passion for Jamaican music and Bob Marley through my mother. She exposed me to artists who inspired my love for the outdoors and my approach to making human-scale change in the world. Bob Marley’s impact through music keeps me grounded and is a little reminder of my culture.

My mother was unbreakable. Still, like many single mothers, she struggled to find and maintain consistent employment and balance the demands of raising children. She worked odd jobs and did all she could to provide for me.

Dad’s incarceration changed the trajectory of my mom’s life. With my father away and other family unable to provide support, she moved to Connecticut to find a healthier and more economically sustainable environment. During this time, she sent me back to Jamaica where my grandmother raised me. I was 8, and it was difficult to leave the life I knew in America, but my time in Jamaica shaped a lot of my world view.

My father has been falsely imprisoned for a crime he did not commit and has been profiled in the Huffington Post among other outlets. He’s become a voice for incarcerated communities during his time in prison. His distinctive perspective and experience directly inform the work I do at JOTF advocating for incarcerated and previously incarcerated populations.

When I turned 13, I entered the foster care system. Entering foster care at that age was frightening. I was moved to a group home in Baltimore County. I witnessed disenfranchised youth whose lives had collided with mental health challenges, merciless abuse and trauma.

My dad was very active at this time in my life. He ensured I was afforded sensitivity and grace and had a special level of care in the system.

At 14, I had an opportunity to leave the group home and went on what is called a “shadow visit” to a couple in an upper middle class neighborhood. The people I met were kind, but I remember talking to my father and expressing my desire to remain in the group home. I felt this sense of solidarity and couldn’t abandon the other girls at the home. I have always had a strong concern for others. I wanted to improve the existence of other girls in the home and I am grateful I stayed.

I attended five high schools while I was in foster care, but am proud that I graduated early — at 16 — and earned a BS in Criminal Justice at Coppin State. Go Eagles!

Is there a particular book or organization that made a significant impact on you growing up? Can you share a story or explain why it resonated with you so much?

A Piece of Cake, a memoir by Cupcake Brown, was gifted to me by a family friend when I was around 12 or 13. It’s a harrowing story of a woman who fell victim to poverty, lost her foundation and family and veered off course to gang life. Later in life, she was inspired to become a lawyer and goes on to make a meaningful impact on society.

When I read this as a child, I found it very affirming. Even as I was finding my way through some dark valleys, this book provided hope and optimism.

From its pages, I divined my own truths and resolved that I, too, would rise above any challenge — however formidable — the world presented me. I knew then that I must create sustainable change in the world for me to be fulfilled with my life. A Piece of Cake was something of a blueprint for the journey on which I find myself today.

How do you define “Making A Difference”? Can you explain what you mean or give an example?

Direct impact, in real life, in real time, at a human scale — that is the sort of difference in which I am most interested in making. Sometimes, minute actions can make the greatest impact. Authentic change comes only by listening intently and allowing people to communicate needs in their own voice. Dismantling inequality cannot come from off-the-shelf services. Rather, it results from relentless, purposeful and bespoke action.

My first job out of college, I was essentially working for minimum wage, and serving as a life coach for individuals with developmental disabilities. This community is rarely seen or heard. My job was to get these individuals on a path to self-sufficiency and stable employment. I found the most impact I had in their lives often came from the so-called “little things”: to laugh with them, to go out in public and not be overbearing. I feel most proud of showing that people with developmental disabilities can be independent and are worthy of love and respect — just like all of us are!

Ok super. Let’s now jump to the main part of our interview. You are currently leading programs at an organization that aims to make a social impact. Can you tell us a bit about what you and your organization are trying to change in our world today?

I am humbled to be part of an extraordinary team at JOTF, a Baltimore-based leading nonprofit organization celebrating its 25th anniversary in 2021. We are led by a brilliant CEO, Caryn York, who is often quoted in the media and sought out for her thought leadership in reimagining workforce development and criminal justice reform policy. She was named a Job Quality Fellow by the Aspen Institute, a Gamechanger by Baltimore Magazine and pens Op Eds in places like The Washington Post. Meeting Caryn and experiencing her magnetism was transformational. I knew I wanted to work at JOTF as soon as we met!

JOTF’s mission is to help low-wage workers advance to high-wage careers. We advocate for real and lasting economic mobility, security and equity and eradicating barriers to educational and employment opportunities. Given the historic unemployment crisis we are navigating this work feels especially timely and urgent.

JOTF has a unique, three-pronged approach to making change. We operate leading edge programs (more on this below), and use the insights we glean from this real world experience to inform and influence our public policy advocacy. Our team works to ensure that policy makers can truly understand the dynamics low-income communities confront. We put our constituents directly in front of lawmakers so we can get to a place where policy making is more sensible and empathetic. The engine that really powers and guides these efforts is a world-class research team that is regularly producing paradigm-shifting research.

After joining JOTF in late 2018, I was promoted to lead JOTF’s program department and today manage our Community Bail Fund and Project JumpStart.

The Community Bail Fund (CBF) is a new initiative and something I helped to co-found and co-create in the middle of the pandemic. It is deeply personal to me. My father’s experience with unjust incarceration really birthed my “why,” and I am grateful to work on these issues. People don’t realize that almost 60% of people in US jails have not been convicted — they are awaiting trial — but ineligible for release due to unaffordable cash bail.

Our Community Bail Fund seeks to dismantle the systemic criminalization of poverty and race by securing the release of low-income residents incarcerated due to an unaffordable cash bail or costly home detention fees. We also provide intensive, customized case management to help the individuals we bail out find the right services — from support to address housing and food insecurity to setting them on the path to realizing their educational and career dreams.

Project JumpStart, a 15-year-old pre-apprenticeship job training program, in partnership with Associated Builders and Contractors, trains Baltimore City residents for skilled, high-wage jobs in the building trades. The majority of participants have had interaction with the criminal justice system and/or were previously incarcerated or housing insecure. The initiative has successfully placed more than 1,000 residents into stable employment in high-skilled, high-wage jobs. The best part is that our grads have this wonderful multiplier effect. They quite literally building Maryland back better. The formula is there, it works, and now we just need to marshal enough like-minded philanthropists (both foundations and individual donors) that allow us to scale this amazing program across other industries, across our entire state and ultimately across all of America!

In addition to my work with JOTF, I am honored to serve on the Board of Advocates for Children & Youth, an organization that creates opportunities for youth in the foster care system. Their mission is incredibly resonant given my own childhood. I want to ensure that youth coming out of the system have access to extraordinary educational and employment opportunities.

Can you tell us the backstory about what inspired you to originally feel passionate about this cause?

My dad’s interaction with the criminal justice system inspired my “why,” and gets me out of bed every morning to work ceaselessly on the issues of workforce development and criminal justice reform.

Jodie Bloom was my social worker while I was in foster care and we remain in touch to this day. It was Ms. Bloom who helped define my “how” — that is, she guided the compassionate, accountable approach I take to making change. She inspired my decision to get into social impact work and made herself available to me throughout my adolescence. She always made sure I received any benefit whether that was grants for college, funding for housing and financial support while I was in school. She visited me throughout college and attended my graduation. Jodie Bloom was my support system, and showed me all you need is one person who believes in you. Every job opportunity since, I have walked in with that same level of empathy Ms. Jodie had for me, advocating for those who are under-represented but still allowing them to make their own choices.

Many of us have ideas, dreams, and passions, but never manifest it. They don’t get up and just do it. But you did. Was there an “Aha Moment” that made you decide that you were actually going to step up and do it? What was that final trigger?

I think mentors — folks who are significantly and continuously invested in helping others realize their dreams — are in too short supply. There just isn’t equitable access to mentors out there for many people. Too often, where we are born and how we grow up exert a real constraint on the people and institutions that we can access.

Nobody has an idea, a dream or whatever and just makes it happen on their own, right? When things truly manifest it takes not only diligence and vision, but also luck, timing and access to mentors like I have in Ms. Bloom.

Ms. Bloom asked me to speak at an event aimed at addressing the community’s demand to shut down the foster care home where I lived. Our neighbors saw it as a stain on their community. I couldn’t stand idle.

I remember being nervous because of the hostility and scowling faces in the room where I spoke. I shared why the group home was created: to house youth who were stripped from their homes for things completely out of their control. After my speech, many community members approached me to share how my comments changed their hearts and minds. Today, the group home is still there and has expanded!

Many young people don’t know the steps to take to start a new organization. But you did. What are some of the things or steps you took to get your project started?

My story is one of collaborative intrapreneurship, meaning I was blessed to combine my entrepreneurial spirit with a nationally-recognized thought leadership organization, JOTF, that shares my commitment to relentless and purposeful action.

My dad’s experience left me with an urge to create a meaningful criminal justice reform initiative. At JOTF I found a perfect partner that gave me the resources and space to co-create something together.

There’s no secret formula, but I think what I’ve learned is that you need to do your homework. Be really intentional about clearly defining a problem, expose yourself to a wide spectrum of ideas that can form a solution and then build a coalition of partners to bring it to life.

Move deliberately, but don’t rush the process of getting stakeholders on-board. Take the time to write-up a strategic plan, but don’t let it hinder you from taking immediate and parallel action to start bringing that vision to life. Expect a process of iteration and commit to testing, refining and optimizing.

Most importantly, be brave and don’t ever give up! Now go out and do it!

Can you share the most interesting story that happened to you since you began working at your company or organization?

My brother was shot and hospitalized in January 2021 while living in Georgia. He moved in with me as part of his recovery. As I was hosting recruitment orientations for Project JumpStart, my brother immediately asked if he could join the program, explaining that workforce development programs are nearly non-existent for young adults graduating from high school in Georgia. And that really hit home. It’s a sentiment that I hear very often from visiting friends and family members. This is particularly interesting as workforce development (job training and creation) programs are most scarce in Black and Brown communities and places like Georgia which has some of the highest minority incarceration and unemployment rates in the US.

Workforce programs are essential to building pathways for stability and economic security and mobility. Joining the military or going to college — those are good options, if the latter is even an option in many of our communities. But people, especially those in low-income communities deserve, the optionality and rich spectrum of choice others in middle to upper-income zip codes have. A massive investment in workforce development programs like the ones at JOTF isn’t a panacea, but it is a proven way to actualize the idea of economic justice for the thousands who never had a chance.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson or take away you learned from that?

Haha, yes, I get a good chuckle when I think back to one of my first jobs as a community organizer working with seniors living in low-income housing.

It’s Valentine’s Day, and I put together what I had considered a romantic dinner for the residents with the works: catered food, balloons, gift bags and roses for each female resident. NO ONE SHOWED UP.

So, naturally, I started knocking on doors. Finally, someone answered, and I was informed that each year our Seniors attend National Bingo Date Night.

I learned to never plan an event without making sure your guests RSVP and are available to attend!

None of us can be successful without some help along the way. Did you have mentors or cheerleaders who helped you to succeed? Can you tell us a story about their influence?

My dad’s sister, Angie, has also been a role model. She is fearless and grounded in conviction. Angie is in the United States Air Force and was constantly being relocated around the country, but no matter the occasion, she was unfailingly there for me.

You name it, she was part of it and there celebrating with me: Prom. High School Graduation. College Graduation. First Apartment. First Job Offer. She was an amazing and reliable source of comfort.

For Prom, she drove down from New Jersey to Baltimore and helped me get ready. From make-up to hair to capturing the moment I walked out and saw my date!

She is a major influence in my life and has achieved extraordinary things. Watching her break barriers and shatter convention has always energized me to do the same. Angie was recently promoted to Chief Master Sergeant — something rare for women in the Air Force and nearly unheard of for Black women. It’s sad — and sobering — to think that of the people who hold that rank, only 1% are Black women.

Without saying specific names, can you tell us a story about a particular individual who was impacted or helped by your cause?

One I am particularly proud of is a young man who joined Project JumpStart out of high school, trying to determine a professional pathway to stability. My team and I were able to provide him not only with extensive vocational training, but also secured a high-paying job for him and provided a grant to help him by his first car. I keep in touch with our graduates regularly and am happy to report that two years since he graduated, he has upgraded his home and car and welcomed his second child. With his discipline and our guidance, he was able to create real growth for himself and his family.

The best part is his story is not uncommon at JOTF. We have achieved this for hundreds of others. We could and should have programs like Project JumpStart in every corner of Maryland and the country!

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

We are a critical inflection point. The pandemic exposed shocking inequalities: horrifically cruel disparities in health outcomes, decades of neglect of our public schools and infrastructure, chasmic gaps in income distribution and a jaw-dropping disregard for essential workers who kept this economy running. At a time when we face so much inhumanity in the world, all organizations like JOTF are saying is: “can we be a bit humane in our policy making and social programs?”

  1. CARE: It’s not hard to both look out for your interest AND exercise real care for your neighborhoods and the most vulnerable. We need community members to be more involved in local politics. It’s literally what’s impacting everyday lives for the working class. Find out who your local city council members and state lawmakers are. Ask what policies they support and why.
  2. ACT: HAVE COURAGE & CONVICTION: In America, we have people who hold jobs, but they live in poverty. How is that even a thing? Does anyone think it is just that 60% of the folks behind bars haven’t been convicted of a crime and are there because they can’t afford cash bail? So, speak up. Show up. Volunteer with your local community organizations. Email info@jotf.orgif you want to help out.
  3. DONATE: Look, not everyone is in a position to do so, especially now. But for those who can, please visit and give as generously as you can.

Fantastic. Here is the main question of the interview. What are your “5 things I wish someone told me when I first started” and why? (Please share a story or example for each).

  1. BE BRAVE: You cannot lead and make impact without Being Brave. You will miss 100% of the shots you don’t take. So, don’t be afraid to take risks. Great success is the product of learning from failures and setbacks. Challenge convention and act with conviction. I grew up in foster care and my mentor and social worker, Jodie Bloom, asked me to speak on behalf of my group home at a meeting with community neighbors who wanted to see our home closed. I was petrified entering this hostile room filled with angry faces, yet, by the end of my talk, multiple community residents and a policeman thanked me for changing their hearts and minds. The home still stands today! After that experience, I knew I would be an advocate and activist.
  2. FIND YOUR WHY + PROTECT IT: To do anything meaningful, you must live with CLARITY and PURPOSE. Being Brave and taking risks allows you to discover your WHY. TAKE RELENTLESS ACTION to become an expert in your field but recognize this requires patience and having a mentor in your corner. No matter what you do, it is essential to have an invested mentor who will challenge and support you. You don’t need to know all the steps to get something done. You just need to stay grounded in your why and work backward from there.
    My dad is my best friend and an ever-present inspiration in my life. He’s been incarcerated, for a crime he did not commit, since my birth. His advocacy for prisoners rights and his journey with a broken criminal justice system inform my why.
    I am UNIQUELY MOTIVATED to lead JOTF’s Community Bail Fund which provides cash bail for those who can’t afford it, so we can stem the epidemic of mass incarceration. I also manage Project JumpStart, a nationally recognized program that trains people, many of whom have been previously incarcerated for high-skilled, high-paying careers in the building trades. Instead of keeping folks locked up, literally and figuratively, they are now engaged in rebuilding our communities!
  3. LISTEN INTENTLY: In today’s social media age, everyone wants to talk. But real progress only comes when leaders LISTEN. The best leaders lead with Empathy. Leadership is actually pretty simple: Listen. Understand what drives people, what needs they have and give them the tools to succeed professionally and personally. Today, I serve people who come from communities like the one I came from to eliminate obstacles to education, careers and economic growth.
    Real and lasting change starts by earning trust, and letting people explain their challenges with dignity. How I speak to those I advocate for is distinct from how I speak to our Executives. ALWAYS KNOW YOUR AUDIENCE.
  4. MASTER THE ART OF NETWORKING: You are your own best advocate. Networking keeps you in LEARNING MODE, allows you to stay FRESH and VIBRANT and advantages you in the job market.
    The most important step is to identify your networking style. If you are an introvert, that may look like coffee/lunch dates or other 1:1 forums. If you are an extrovert, like I am, that may look more like attending networking events and coordinating your own programming and experiences that will bring folks to you.
  5. MENTAL HEALTH IS ESSENTIAL: The pandemic has increased anxiety and stress, particularly in the Black and Brown community. You will not be able to help others until you take care of yourself and engage in mindfulness and wellness. We are living in one of the most overwhelming periods in human history. I spend my day listening to other people’s struggles.

In order to provide them effective solutions, I need to have peace in my mind and clarity to think quickly on my feet. The best way I can show up and stand up for the people that I serve is by engaging in self-care and meditation.

If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

Anyone can make a difference. When you set out to make a change in the world, create generational impact. Be methodical and seek ways to transform systems so the change you make will be felt across generations. What others did before us impacts the way we live in today’s society, and likewise our younger siblings, children, and their children will be left with the impacts of the legacy we leave behind.

There has never been a better time to be an effective change maker. The current climate has created a real movement, a groundswell of interest in social justice.

Do some homework and commit yourself to real diligence. Pick your thing, be intentional and start volunteering! Your time and ideas will positively change your community and society, so don’t procrastinate!

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

This is your easiest question and has one resoundingly clear answer: Brené Brown. Brené Brown has been a huge source of inspiration. I’ve never met her, but I read and watch her religiously and I feel like she’s been a part of my life. I’m a superfan. She’s the Huffington Foundation Brené Brown Endowed Chair Professor at the University of Houston and a decorated author and speaker whose insights about empathy and courage have informed my style of changemaking. She’s badass.

I cannot adequately put into words what it would mean to meet Brené and introduce her to what I am working on at JOTF. It would be an honor to show her Baltimore, a beautiful and vibrant city, and the most underrated food and beverage city in the country!

How can our readers follow you online?

Follow JOTF by visiting the website and checking us out on Instagram, Twitter, Facebook and LinkedIn. And, by all means, if any of your readers want to reach out, please send me a note at

This was very meaningful, thank you so much. We wish you only continued success on your great work!

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