January 18, 2024

Episode #116: Jacki Leahy – Activate the Magic

Jacki hails in Boston’s Back Bay with her miniature dachshund, Freddy. Formerly a kindergarten teacher and Manhattan apartment broker, she took a bold leap into the dynamic world of tech startups in 2015.

Over the past 9 years, Jacki has adeptly navigated the chaos that often accompanies the pursuit of building a repeatable sales motion. As the tenth hire at LinkSquares, she led the construction of teams, processes, and systems that propelled the company’s ARR from $350k to $9M in under 2 years. This transformative journey ignited her passion for Salesforce and RevOps—essentially, all technical infrastructure supporting marketing, sales, and customer success.

Now, as the founder of Activate the Magic, a boutique RevOps agency, Jacki empowers B2B founders and sales leaders with scalable tech solutions for chaos-free operations. Her expertise lies in Salesforce migrations, renovations, and integrations—addressing all the crucial components to liberate leaders from operational minutiae and provide a clear pulse on the business through reliable leading indicators, forecasts, and comprehensive pipeline overviews.

At Activate the Magic, all clients enjoy month-to-month agreements, a testament to Jacki’s commitment to delivering recurring impact. If you’d like to connect with Jacki, book your complimentary coffee chat at https://activatethemagic.com

In honor of the fellow business owners in your life that had an impact on you
becoming the person you are today, let’s celebrate them. Click this link to apply to be on our podcast to recognize those people: https://www.BeMADTogether.com


you’re listening to the self-made is a myth make a difference together show with your host coach Tim campsa where we talk with successful business owners to hear the stories of their Journeys in building their successful businesses and more importantly we recognize the folks who help them Excel because we know that achieving business success is not something we can do on our [Music] own hello everyone this is coach Tim campel and I’m excited to have a fellow business owner from Massachusetts with us today check this out my guest studied abroad in Germany having only taken one semester of of German before she went there and and had a full course load and had to write reports and all that crazy stuff and only failed one class so wow we’ll get her to share that with us a little bit here in a minute in her downtime she enjoys bringing her dog Freddy to the woods and the beach and letting them run free and she’s most proud of the Gritten commitment that it took to land a job after she was fired from her first tech startup so we’ll get her to share a little bit about that as well it’s my pleasure to welcome Jackie to the show today hello Jackie hello Tim it’s good to be here well hey let’s start with having you um introduce yourself tell us a little bit of your personal story like where you born and where you live about your family and hobbies yeah um so I’m Jackie Ley uh I’m from outside of Boston draid and Carlile um I went to UMass ammer go Minute Men and after college I became a kindergarten teacher I did Teach for America for two years and then an extra year um and then once I left the classroom I kind of bounced around it was coming it was about to be 2008 so things were a little wide um and I ended up being a real estate agent in Manhattan so I was running around the city going showing people apartment breaking into some you gota do what you gotta do um and in 2015 I kind of was like bored like I’ve conquered it like check um with with real estate and I really wanted to go into the tech startup World um and so I started entry level bdr that’s the entry level sales as a as a 33y old in a tech startup um and it was tough but you know what I I’ve discovered I loved outbound cold prospecting and eventually just became obsessed with like the tech stack that enabled me to do that um found Salesforce and went head over heel for Salesforce um and I about a year ago I started my own uh Consulting agency so we do fractional Revenue operations Consulting it’s mostly for the Salesforce ecosystem and Tech startups fantastic and tell us about Germany so you decided to go there without really speaking German that’s Brave yes I wanted to go to Russia but my parents wouldn’t let me so so I picked a different language that I didn’t speak yet um and it was beautiful I made so many friends um and I learned enough German to make friends and like make people laugh like puns right and at that once I once I accomplished that I was like okay enough with the grammar that’s it that’s all I need to know that’s awesome so tell us I’m sure there is because you’re you’re just full of uh laughter already is there a funny story that your family likes to tell about you that you’d be willing to share with us today I’m willing to share it as long as it doesn’t you don’t nobody comes back and haunts me about it don’t worry it’s not recorded or anything like that so it’ll be fine when I was little you know apparently when you’re little you really don’t get like sarcasm until like later and my dad did the gotta nose joke and I was horrified like I viser remember this and like I must have been touching like my nostril and I started crying like there’s a shaking and like to this day to this day that is fantastic I love it so tell us how’ the business come about at what and at what point did you have the confidence that you could run your own business oh my goodness so I had been in the Consulting space for like three years and I was with winning by Design which was like my absolute dream job I am obsessed with the founder um he has the his name is jao Vander Cru and he he does the bow tie like the the funnel and then the it looks like a bow tie it’s like math medical first principles on subscription business models um and I was going to start the revops Consulting offering um and then it was it was 2022 and bester Ventures is now calling it The sassacre everything just went sideways everything went sideways I I couldn’t make heads or tails or get any traction and ultimately they’re like this doesn’t make sense anymore any more so you got to go um and which was a bummer such a bummer right like H um but my friends were like Jackie you’re a you’re a baddie like why don’t you just go into business for yourself yeah um and it really was they were the ones who completely reframed everything for me so I was let go on a Tuesday super sad um but then brought back to life by my friends on Friday and it was my like other Salesforce nerd friends like we have a happy hour on Friday afternoons we’re called the best friends Club um and they just like deflated me um and I started my new company the following Monday so like less than a week and I had my first client pay like paying client like 10 days later wow yeah fantastic so so cool like it ended up being the absolute best thing that could have ever happened that is amazing so tell us more about the company what’s the name what do you do how do you help people yes so it’s called activate the magic um and personally I just am obsessed with human potential like I know that every single human is sitting on a pile of gold in just Brilliance um and it’s really just about like activating that right um so activate the magic I may or may not be a little bit of a [Laughter] witch um and so I started just you know solo practitioner um but like thank goodness thanks to my near decade of being aggressively helpful in slack communities and on LinkedIn and other communities um I ended up generating clients like real fast where I had where I like had to bring other people in so I accidentally started like this revolutionary Consulting agency um so it’s been like a little over a year so it was August of 22 that it started um so and now we have like I have a business partner I have 10 subcontractors we’ve got a whole handful of clients and we’re we’re creating a different way to do the old sales Force Consulting thing it’s so fun that’s awesome so when you say different give a little bit of context how are you how are you different or how are you helping people in a different way I hate the billable hour my name is Jackie and I will go on record I hour and I think statements of work s so’s es especially especially in the nook of the world that I am in just do not make sense because by the time you actually get in there and pull things apart Heart Like priorities shift things hit the fan and like it would waste so much time to go back and forth and renegotiate whatever s so we had come up with um so I said why don’t we do a subscription and we’re agile and it’s and like no I don’t want anyone to feel like they’re only working with me because they signed something and they have to like legally B me right so it is month-to Monon subscription um and so we still do use like the the hour thing but it’s really more of like a a unit of of impact so we have small medium or large packages um the small starts at 4K it’s like four hours a week um medium is 6k and six hours a week and large is 10K uh 10 hours a week and it’s really we get to right size the support for the client and it’s only a one month minimum okay and my clients go up and down in the packages as well sure so if there’s like a actually this board meeting is coming up and we actually want to redo how we’re doing this process we can bump up to a large for a month get it done and then pop right down to smaller medium um yeah so it’s like I I I want the client to know that I’m like aggressively on their side for everyone listening make sure to check out the company in the link in the description and go visit Jackie on LinkedIn and let her know that you watched her interview thank you yes I love LinkedIn I it’s so fun so so Jackie tell us a story where someone pushed you or inspired you that you could do it maybe even you when you didn’t think that you could and the impact that that person had on you yeah yeah um so Brad Smith is the founder and CEO of a software company called sonar um it’s a specific tool that’s super helpful for Salesforce admins and it teams um and he was the one who actually built the the revops community it’s called wizards of Ops community that um I’ve been able to make all these friends with and he happened to be on that happy hour that I was on um I was actually traveling so I was in a hotel room I had the the shades drawn I had the lights off I was going to take a nap and then I was like you know I should just just let my friends know that I’m in a funky place so I hopped on and everything changed and Brad was like actually let’s start a pool who who like I I bet I will put money down that Jackie will have a new job in seven days right so it just shifted the whole thing um and and since then he’s just been wildly supportive um he’s connected me with one of one of our leaders in the company his name is Jacob um and one of our favorite clients grayscale um so he’s just been like one of those magical forces in my life and just so grateful for him that’s amazing that uh that you weren’t going to go on to the call and then decided reluctantly decided to and then wow bam yeah yeah because like I’m kind of known for being like happy right like sure and so it was I can’t imagine why people would think that no it’s a it’s a real head scratcher but like I was sad I was boned and um I’m so grateful that I had the support system that had I felt so supported such that I could go on as my as who I was in that moment and yeah I I think that’s a good lesson for all of us to internalize right of you didn’t want to do it because you needed it right sad but you didn’t want to because you think you thought you’re supposed to be happy all the time but you really needed some encouragement and then when you opened yourself up to it wow there it was that’s amazing yeah so thinking of of learnings and all the stuff that you’ve been through as you’ve been building this business what’s what’s your biggest learning as a business owner I think really leaning into trust and transparency um I it’s a journey right like I I really want to make everyone happy all of the time um and like not like it’s it’s it’s a learned skill for me to actually um push back against things right and introduce friction like my not just my personality type but my literal career is all about eliminating eliminating friction yes so to like willingly not go with the flow and add friction right so um my now business partner how that happened was she wanted to negotiate a bigger split for the project she was running and like of course like she’s freaking brilliant like she should get all the money she should get three times the money that we’re charging like yes I agree but then like but there’s only so many projects that Heather can lead right so she had to like Max I could give her one more but like what what the world actually needed was for her to to share her Brilliance with the rest of the team and like what if she was really the technical architect leader of the whole gang right so she would be less Hands-On keyboard and like in weeds but but have a bigger impact on more companies so like actually I came back and was like what if what if right like I in instead of like this project getting a bigger split on what if you become a partner in in like the profit yeah right so and that was scary because up until then like I was really only like accountable to myself MH right like of course making everybody happy but like if you want to go fast go alone if you want to go far like go together and so it’s like risky it’s risky it’s vulnerable um but ultimately it’s been so freaking rewarding this lady is amazing and such a great match for each other and um but yeah that that was probably the biggest biggest scariest step yeah what a great segue into my next question because we know that business success doesn’t happen in isolation so tell us about your biggest challenge as a business owner and maybe another business owner who came alongside you and helped you through that it’s really [Music] um along the same lines um but like negotiating pay tell us cut and it’s like I want everyone to earn a maximum rate but that slows everything down right so it’s like giving up like being a dictator of a Utopia right setting that down and being real with people like hey like I want you to make 125 an hour and the reality is that you’re not going to get put on projects at that rate right to you know and I would credit actually Alex heroi for this like having a season of learning versus season of earning and recognizing that I had been in a season of learning for a very long time and so it’s not outrageous for me to promote expect enroll people in their season of learning I love knowing like having the confidence in the people that I’m picking and how we’re structuring it that that the learning is actually part of the compensation like if you were earning your maximum hourly rate No One it there would be no need reason logical path for anybody to pour into you yes wow it’s interesting that um you think of folks who come across as I don’t want to you know I’m not getting any benefit out of being here or I’m not there isn’t this isn’t going to help me later so I just it’s all about money but the reality is like the types of experiences that they’re getting and the the types of projects that they’re working on can in in some cases be very unique to you know being working with you guys and and being able to be exposed to that stuff that they they wouldn’t otherwise so yeah there’s there’s huge amount of value in that in in terms of who it it helps them to become right yeah yeah um but it also has me on the hook for delivering that value fair enough yes right yes and and you you kind of alluded to it earlier and it can be very lonely at the top trying to navigate all of that stuff right of provide awesome service to your clients while also juggling all the internal Dynamics yeah and knowing that people can punch up but not punch down right knowing that I am going to be the villain in some stories absolutely right yep because at the end of the day you have a business to run yeah you don’t have a you don’t have a bunch of friends to take care of you have employees to manage to make sure that the business is profitable and sustainable so that those employees keep getting a pay Jack yeah and navigating a tough conversation around I know you think this isn’t fair but that’s not what’s important yeah right yeah what’s most important is the client the impact the client experience like that is what we’re that’s what we’re refactoring around like yeah and owning it and and knowing that is all my fault like like I messed up like I didn’t set the expectations I did it for you know um and not only not only owning it but then working through and saying okay and here’s here’s what I need to do to to correct it or fix it and then be bold enough to to actually execute that plan and stay strong because you know it’s the right thing long term for the health of the business yeah and you’re gonna ruffle feathers and you’re gonna frustrate people and just knowing and embracing that that’s part of the journey it’s not intentional but it’s just gosh yeah and like leaning into like please I know you’re mad like you can tell me right like and mean it like it’s one thing to be like my door’s always open like I’m open to feedback which is easy to say and it’s confronting to actually do so yeah and and what we really want to say but we know it doesn’t make any sense is I’m open to great feedback please come and tell me how wonderful I’m doing praise me as often as you’d like so Jackie I’ll put you on the spot here if I used to ask you to pick three people in your business owner Journey that you’re most grateful for their help in your business’s growth who are those three people and how’ they help you Heather Sans she’s my business partner um we actually worked together at a boutique Salesforce agency a few years back um and you know she would she was always so brilliant like technically just detailed and just ah and she had always been so generous with her wisdom and would hop on and help at any time um so I’m just so grateful to have her confidence and team mate as a teammate um I’m so grateful for um one of my early clients um his name is Abe and it the project could have gone smoother right um and that was really one of the hey I’m doing my learning out front like let me be transparent about what I’m seeing seeing about how I messed up um please pour salt on this wound and and show me your perspective of what the impact was that and move forward with me as a like a lifelong Advocate right for each other um and um my parents my mom and stepdad Ellen and Mark um I’m going to cry um they had always said especially my stepdad like always related to me as an entrepreneur um and I was like I was always no no no no no um and recently I said to him like I’m just now realizing that I wasn’t a problem employee I wasn’t difficult to manage I wasn’t that I was actually a brilliant entrepreneur um I love that mindset shift that’s awesome yeah yeah yeah it’s um the mindset is huge right it’s it’s more than 90% of whether we’re going to be successful or not so I like how you took what what we could do and right beat ourselves up and say I I just must not be cut out for this and realize that I’m cut out for so much more in a different role yes good for you yes and like there isn’t a hierarchy yeah right when we when we’re real and honest with one another as business owners right it’s like yeah we’ve all been through the same you know beat ups and got the same scars and scabs and and it’s just it’s part of the journey and when we’re willing to be real and authentic we can learn so much from one another it’s like oh yeah you went through that too how did you handle that and we can grow and learn from one another yeah yeah absolutely there’s way too much um stuff on social media that makes it sound like we you know people are overnight successes and they got there on their own that’s the whole reason we have this podcast to yeah you know to dispel that because it’s so damaging when when you read that stuff and go oh wow look at they are all awesome and I suck yeah oh my gosh yeah and there’s a lot of that um you know well what am I doing around Jackie you literally made one LinkedIn Post in you have a whole company now it’s like right that is a perspective that is accurate right and if you pan out right zoom out this is literally like a blip right but let’s let’s look at the 17 years of struggle right like I’ve been fired so many times I’ve like made a fool of myself I’ve you know been probably spending too much time helping other people or learning like sure it’s been a fullon court press for decades yeah yeah so let’s let’s shift gears to the Future as you think about the next three to five years what’s the biggest challenge that you see that you’re going to face in reaching your company goals and who are the types of people you’ll need to solve that um so we’re at like 700k annual occurring Revenue AR um I’m playing for 2 million by the end of but by 2025 nice that’s as far as I’ve gone like visionwise um and the people that I’ll need are are other people who see the opportunity to create a new way of how we relate to each other at work so what do you see as the biggest challenge of of getting there so more than doubling your your Revenue what’s going to get in the way what do you what do you think what are you anticipating quality control on humans yeah right taking the time to like finding the right people yes um luckily I have a really huge network of like amazing like world class Talent like adorable humans right but it’s also like a constant game of enroll en rolling others in the vision and and enrolling them in themselves enrolling them like into being like vulnerable and leaning into the feedback and standing for something big um it’s some days it sucks right I and I really want to be like well if if they would just take some initiative like how would you think that it’s like well that’s that might not be the most reasonable thing so really like creating systems um that really support as as we grow um it’s awesome yeah and unpacking what it is that I do right like the unconscious competency and the like he our choosing to believe that everything is a SK skill right like um like that human touch and that empathy and stuff those are actually skills yeah absolutely and building and training and rewarding um yeah can’t shortcut that the the the vision and and culture is is so key and yeah the mistake a lot of us make is we don’t give it the the attention and the the time that it needs because people enroll to to use your word people enroll when they believe in something bigger than themselves and they want to be part of something bigger than themselves and and so investing that time to right pen to paper what is the vision what is the culture you know what what are our values and our beliefs what does it feel like to be part of of this company so that and then and being in true to it right and holding one another accountable not just printing it and putting it in a binder but you know bre coming back to it weekly or monthly and and checking in on one another and say hey are we are we truly living this and breathing this and right are we being are we being honest to what this piece of paper says yeah and there’s not like a like a onetoone correlation between effort in that department and revenue no no you however there there’s no there is no mathema iCal correlation but there’s 100% correlation right yes yes yeah yes so it’s it’s it’s very challenging to justify investing in that yeah but it is absolutely mandatory to invest in that we’ve all been in companies where there hasn’t been a defined culture or people were hired that weren’t a good cultural fit and we all know what that feels like right so we know how important it is but it’s hard to to calculate the ROI and therefore be able to justify it being in the budget yeah Jackie last question Jim ran an awesome business Guru one of his quotes is we become the average of the five people that we spend the most time with so what advice would you have for for new business owners who are trying to do it on their own well that’s dumb don’t do that um my advice is to find your North Star person right and it doesn’t have to be your Northstar person for the rest of your life and the rest of their lives it can really be like for this chapter in my life my Northstar human is Alex heroi right like so I’m going to actively look out look for people who have those traits who hold me to the standard right so like the easiest like yeah put myself in the environments and Social Circles where it would be it would be less reasonable for me to not have the outcome yeah I love it I love it so um a lot of folks will will say things that I’ve heard well I don’t want to bother them I don’t want to ask and because they’re probably really busy what H what would you say to that um well check yourself before you wreck yourself right like if you if you send me a LinkedIn message being like hey I’d love to pick your brains with the calendar link I’m going to be like no thank but like hey um Tim the the way that you talk about um standing for leadership was super inspiring I would love to hear more about that Journey um would you be game to hop on a 30 minute Zoom with me right yes right like the acknowledgement that’s that’s my ultimate magic trick right acknowledge acknowledge acknowledge like say the things that people usually say for their funeral yeah yeah because here’s the thing right is where I think you’re going is we all like to be appreciated and valued and we all like talking about ourselves so everybody’s being genuine and saying hey I think you have some really cool experiences that I’d like to hear more about right and there’s no sniff of it being a sales pitch right or a B witch right I was like totally I’ll give you a half an hour to talk talk about me that would be fantastic yes yes Jackie sounds like you’ve been blessed with some awesome people in your journey if they were all here on the show what would you want to say to them you’re the best thank you I love [Music] you hi FBS all around um and truly like we’re here to create lives of our wildest dreams and just I appreciate you and I acknowledge you for standing for me to be and live the greatest version of the grandest version of myself so thank you yeah I love it Jackie it’s been a pleasure speaking with you today thank you so much for being on the show thank you for having me I got to talk about myself for like a whole half hour thanks for listening to the self-made is a myth show with your host coach Tim campaw please help spread this Movement by liking and subscribing to our show and following us on Facebook and Linkedin or wherever you listen to your favorite podcast to join our movement go to bead together.com okay folks that’s a wrap please pay it forward and be sure to tune in next time to the self-made is a myth podcast