“You have the coolest job in the world.”
I know I do. And I’m very blessed to have it. Today, I want to share with you my journey of coming to Hallow, what the last five years have been like, what I love, what I don’t love, and where I hope it goes from here.
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For those who don’t know, Hallow is the #1 prayer app in the world. With over 1.5 BILLION prayers prayed through the app, it has had an immense impact on the life of the Church and the world at large.

My Journey to Hallow
My journey to Hallow really began when I was 13 years old, which was 11 years before Hallow was founded. In 8th grade, I decided to join the Catholic Church, becoming the first Catholic in either of my families. I went from my Catholic grade school to my Catholic high school, where I met a boy who would become one of my best friends for life.
His name was Alessandro DiSanto, the Italian stallion of my high school friend group. Alessandro, or Sandro as we called him, was at the top of our class (#2 to be exact, a fact we don’t let him forget), played soccer, played music, and was a favorite of all of our teachers.
I, on the other hand, earned myself 21 detentions in the first two years of high school, along with an in-school suspension to top it off. This all paled in comparison to the legal trouble I risked getting myself in on a regular basis. From taking illegal drugs to school to joyriding without a license, I was living on the wild side while Alessandro studied hard and spent summers at programs for prospective students at Harvard.
And yet, in our free time, we spent a lot of time together. More and more every year, leading to a deep bond that continued through college and beyond.

We visited each other at our respective colleges and in our early careers in the heart of Manhattan and at Fort Benning, GA. I’ll let you guess who went where.
We served as groomsmen in each other’s weddings and are now honored to be godfathers to each other’s children. I think few people are blessed with the type of friendship that he and I have, and it is not one that I take for granted.
I know this isn’t a reflection on friendship, but I’m going somewhere with this.

I began my career in the Infantry. Alessandro attended my Ranger School graduation. Then I went on to serve in the historically awesome 82nd Airborne Division in Fort Bragg, North Carolina. I deployed to Afghanistan, and we stayed in touch. Upon returning from deployment, I remember Alessandro floating the idea of starting a prayer app with me during a casual phone call.
I thought it was awesome—something that could really impact a lot of people’s lives. After all, my journey from a habitual rule-breaking teenager to a faithful Catholic was made possible largely due to the gift of prayer. It absolutely changed my life. And I knew most people did not know how to do it, especially in any meaningful or transformative way.
He goes on to quit his job to go all in on this thing—an idea that we all thought was crazy at the time. I decided that year, in late 2018, to get out of the Army the following year. Hallow launched in December of 2018, and they were off to the races. At this point, I never thought working for Hallow would be in my future.
I took a job as a Parish Consultant at the Dynamic Catholic Institute. I absolutely loved it and thought I’d work there until my death. Funny enough, I never made it to my one-year anniversary. This was mostly because of two reasons:
The Dynamic Parish program was ending as we knew it. I was offered a job in Development or a severance package. I took the latter because
I met a very special lady who would become my wife. She lived in Atchison, KS (yikes), and I knew if I took the Development role there was a high likelihood that I’d rarely get to see her, let alone actually discern marriage.
This led to my greatest act of sacrificial love in my lifetime—moving to Kansas to date my future wife in person. I took a job at the incredible Benedictine College, which came with a generous 53% paycut. The downgrade from my beloved Cincinnati apartment to a rugged combination of freshman dorm rooms, wrongly referred to as an apartment in Newman Hall, was the greater sacrifice. But now I have kids, and we’re happily married, and yada yada yada, it worked out :)
But it most certainly was not my long-term career. I love Benedictine College, but that year was the worst year of my life since Ranger School. I missed the two weeks of training due to my start date, Covid rules had to be enforced, I missed homecoming for Alessandro’s wedding (worth it, did you see the photo?), and tore my achilles playing basketball with students in January.
After those wonderful six months, I was ready for my next move. I applied to the Augustine Institute and was offered a full scholarship and a job. Finally, it felt like my future Catholic career was back on track. I called Alessandro to give him an update on my life. He suggested a phone call with Alex Jones, CEO of Hallow, whom I had met several times by now.
Alex is incredibly to the point. After a few minutes, he hit me with, “Why don’t you just come work for us?”
I paused, utterly confused. “Uhh, and do what?” I said in reply. Mind you, at this point in my life, I’m an Infantry Officer with 18 months of experience in ministry. I have no idea how a start-up works, no knowledge of software development, and a voice not nearly as sexy as Francis’ (if you know you know). Therefore, I have no clue what I could possibly contribute.
“We’re starting a sales team”, he told me. And I immediately lit up. Now THAT I can do!! I was over the moon. Luckily for me, Hallow was still very uncertain and just crawling out of the “only our friends want to work here” stage. I don’t think I’d ever get hired here today, especially not just off the street like I was then.
So that’s how it began—I was the first Sales Lead (now Partnership Executive) at Hallow, starting in July of 2021. I was the 18th employee at the company and the third on the B2B Team (the other two pictured below). Alessandro became my boss. And our goal was to partner with schools and parishes to accelerate both Hallow's business growth and its mission.

My Career at Hallow
The last five years have been nothing if not insane. I had an unfathomable number of things to learn. What is ARR? How do you best structure a sales call? And what in the hell is an illo? Hallow seemed to have its own language—mirroring the Army's culture. But here, there was no ROTC or any real onboarding. I was immediately seen as a leader, especially after we started hiring more people in the coming months, who looked to me as a veteran on the team despite not being halfway to my one-year anniversary.
We had some solid growth in the first two quarters, then got absolutely annihilated for two quarters. I started updating my resumé and casually applying to places. I even had an interview. We were seriously wondering if this whole B2B sales thing would work at all.
The panic was followed by great success in the second half of 2022. Things were really picking up steam. We made some incredible hires in 2023. We started working more intentionally with parishes. Then, in 2024, my role really began to change.
I was promoted first to Senior Partnership Executive. That summer, I was made the Associate Sales Manager. I held that role for about 9 months before being promoted to Sales Manager and entering full-time leadership. About 9 months after that, I was promoted to my current role as Senior Sales Manager, where I now manage Regional Sales Leaders, who manage Partnership Executives and the overall sales of their region.
One of my greatest career desires has been to do something only a small percentage of people can do. Anyone can take orders at McDonald’s. Most people can do basic corporate jobs. Even after a few years as an Infantry Officer, I came to realize that our time of war was coming to an end and that the Army didn’t really need Nathan Crankfield.
In contrast, my current position fully checks that box. I’m certainly not the only person who could do it, but I think I’m one of only a few who could do it well. It requires a unique combination of leadership skills, passion for the Church and her mission, and a love for sales and business development.
That is not something I take for granted.
The B2B team of 3 has grown to 70, with much more expansion ahead of us.

The Good, The Bad, and The Ugly of Working Here
First, I’ll answer the general and most common question I receive, which is: What has been your experience working at Hallow?
Then I’ll hit you with some more rapid-fire FAQs.
I do not exaggerate when I say that Hallow is the greatest company in the world. While the two men pictured above (Alessandro and Alex) drive me absolutely nuts sometimes, they, along with the third cofounder, Erich Kerekes, have built an absolutely incredible company. Their leadership, vision, and example have created a culture that I believe to be second to none.
They seek to create a job that will be “the best job you’ve ever had and the hardest job you’ve ever had”. Alex has made it very clear to the team over the years that he did not seek to make the best Catholic app in the world, but rather one of the best apps in the world, period. We don’t want to just be the best Catholic company in the world, but the best company in the world.
Plenty of people will say we are not that, but it is the goal. And while I haven’t worked at every company in the world, I do believe Hallow is the best company for me and for people like me.
What I love
I chose to join the Army because I wanted to become an Infantryman. I chose to become an Infantryman because I wanted to go to Ranger School. And I wanted to go to Ranger School to see if I had what it takes to be elite.
Most veterans struggle in their post-military careers because they lose their sense of mission, purpose, and teamwork. And many of us miss working with a fully dedicated team that seeks to maintain really high standards. I am blessed to have found all of these things at Hallow.
Our mission is to help people pray. And we’ve been able to, by the grace of God, do that on a really large scale and in a really deep, sometimes life-saving way. We’ve received countless testimonies and hundreds of thousands of five-star reviews that recount how Hallow has helped save marriages, break addictions, and end suicidal thoughts.
We have kids who tell us they now believe God is real as a result of praying with Hallow in their classroom. We have parents who say they’ve never felt closer to God and to their children since learning how to pray with them through the app. One parish reported to us that 25% of their OCIA class this year said they were there because of Hallow.
Outside of the priesthood, I don’t know how I could have found more meaning and purpose in my work.
That being said, you can do great work for the Gospel and for people in many roles in the Church. What sets Hallow apart is our true commitment to excellence. Many ministries and parts of the Church operate more as a government bureaucracy than a fast-moving startup dedicated to success. It’s the difference between being in the Army Rangers and working for the IRS. Both are government jobs. One is ruthlessly committed to high standards and accomplishing the mission, while the other is a place where many people go to collect a paycheck.
Don’t get me wrong, there are many incredible people doing amazing things in the Church. But some of you who have worked for the Church or a nonprofit know exactly what I mean. Dynamic Catholic, in my opinion, is in a pretty high tier in this regard. It was hard work there, but it wasn’t this hard. And I really like hard work, which is part of why I really like Hallow.
Lastly, the culture that this creates is also really amazing. This is especially true on our sales team. We can earn a great income from our work while serving an incredibly important mission. Usually, people see those two as opposing each other and accept that they have to choose one or the other.
One bonus one: I can’t lie, I love the prestige of it all. Hallow is the New York Yankees, the Los Angeles Lakers, or the Dallas Cowboys of Catholic organizations. When I worked for Dynamic Catholic, most practicing Catholics knew of the organization or of Matthew Kelly, its founder. But roughly 13 non-Catholics are aware of the company.
Working for Hallow is in another statosphere. Whether it’s at the gym, on a flight, or at the barber shop, it seems like half the population perks up with recognition when I tell them where I work. It’s awesome.
What I don’t love
I have a love-hate relationship with working for a startup. If you’ve ever watched the dramatic television shows or movies about the early days at Spotify, Apple, or Uber, you get a sense of how hectic life at a startup can be.
Many jobs say they’re fast-paced, but few really mean it to this extent. Going from a 250-year-old organization like the Army, filled with rules, regulations, and set expectations, to something like this has been the ultimate whirlwind. I love it for all the reasons I listed above, but it’s not without its challenges.
Some people simply don’t like that we don’t have everything figured out. We change A LOT of things very frequently. These constant pivots can cause emotional and mental whiplash, which can be quite unpleasant. We constantly face new problems and communication breakdowns. We scale too fast and still have pretty crappy onboarding after all these years.
Hallow expects a lot out of you. This is not a place to come get a remote job and coast. We don’t track your hours or see if you’re constantly online from 9-5. It’s an organization for adults. We expect great work from you, which, especially on the B2B team, is pretty easy to measure by your results.
If you simply love Jesus and want to work somewhere that “aligns with your values”, this probably isn’t for you any more than Navy SEALs’ hell week is for people who love the beach.

Frequently Asked Questions
Do I have to be Catholic to work at Hallow?
No, you do not! We actually have a pretty diverse team when it comes to religion. Most are Christian, but there are certainly non-Catholics! Should you become Catholic? Yes, but that’s a topic for another time :)
How does Hallow’s mission show up in the day-to-day work culture, or does it just live in the marketing?
We pray together. We celebrate Mass together when we’re in person. We have daily rosaries together — all of which are optional. We also have an annual spiritual development stipend, which is extremely generous. We get free tickets to the bi-annual Summit. Hallow offers exceptional benefits, including baby bonuses, unlimited PTO, caretaker leave, bereavement leave, and more.
Is this a stable company or an early-stage startup where my job could disappear in six months?
Nobody has ever lost their job in six months except for serious underperformance. At a startup, the future is definitely unknown. But that’s true at any company or in any industry. I feel very comfortable in my job security and think most strong performers feel the same.
What does compensation look like compared to a non-mission-driven tech company? Am I taking a pay cut to work here?
I think it’s true that many people here could make more money elsewhere in the secular world and that very few, if any of us, would make more in the Catholic world. Software developers at X make more than ours, and probably work 3x as many hours. Most people working in parish life probably make less than our parish leads. So it’s somewhere in that range. Illinois law requires we post the pay scale of each role in the listing, so it’s never a secret!
Is this a remote, hybrid, or in-office environment, and where is the team actually based?
We have an office in Chicago, but nearly every role is offered remotely. The exceptions to this are most commonly on the international team, where you do need to live in the country you serve most of the time. Our B2B team is national, but we becoming more intentional at hiring people who live in the region where they will work.
What does growth and career development look like here? Is there a real path upward, or does the small team limit that?
It is my personal belief that we are just getting started. I think there is plenty of room for growth at Hallow, but that also looks different for every role. On B2B, we have a long way to go and many leadership opportunities. If anything, we’re trying to avoid promoting people far before they are ready for more responsibility. And we heavily prefer to promote from within.
What is the leadership team actually like to work for day to day? How accessible are the founders?
When I worked at Dynamic Catholic, I was legitimately never introduced to Matthew Kelly. At Hallow, every one of my employees has a monthly meeting with our CEO and our team of 15 to share their learnings and concerns, or ask questions. Our Head of Sales and CFO are also extremely accessible. Everyone is reachable via Slack if one prefers a private conversation.
How do you balance the commercial pressure of being a venture-backed startup with staying true to the mission?
This really isn’t as hard as some make it out to be. When we accomplish our mission of helping more people pray, we also grow as a business. I am personally a big proponent of morally strong Capitalism. I think that people with well-formed consciences can do great things for the world while becoming extremely profitable. The two don’t often contradict each other.
But they might sometimes. Hallow is most often criticized for trying new things—and we will never get it 100% right. You have many Monday morning quarterbacks who evaluate a decision long after it has been made and deem it unacceptable. Hallow tries new things to carry out the New Evangelization. Mistakes are inevitable, and we always strive to learn and improve from them.
Can you connect me with “x” person at the company?
Honestly, probably not. We receive a lot of applications. Like, an insane amount of applications. I recently went on our applicant management system and saw this:

48,000 applications all time. That works out to 6,400 per year — and they really didn’t hire anybody for the first 2.5 years, so it’s closer to 9,600 per year. That’s about 26 a day. It’s an amazing gift, but it makes hiring really hard. I appreciate your effort to reach out via LinkedIn, email, or text to those you know.
We really aren’t trying to be rude when we decline your request for a call or connection. One summer, we had 7,000 applicants. I legit could’ve made a full-time out of the requests I got for 30-minute phone calls to learn about my experience at Hallow. That’s why I spent 2-hours writing this article to help save the several hours a month I spend on those phone calls.
How do I make my application stand out?
If you majored in the Psychology of Sea Turtles and have worked at Starbucks the last few years since graduation, I really don’t know what to tell you.
If you have relevant experience and a real desire to work in the role you applied to, here is what I honestly think helps people stand out when I’m sorting through 500 applications:
There are two questions at the top of each application. The first is “Why do you want to work at Hallow?” The second is “Why are you a good fit for this role?”
This is my personal perspective, but I see the first question being about what draws you to Hallow’s mission, culture, and structure. If you just list things about you, then you’re kind of missing the boat. It’s a place, especially when applying to a sales role, to sell me on your love for Hallow. This will drive your success in sales, so it’s very important.
The second question (again, just my opinion) is where you begin to sell yourself. Why are you a good fit for this specific role? The question is not “why are you a good fit to work at a Catholic company?” Therefore, telling me about how important your faith is to you is insufficient. That’s a great thing to hear, but that doesn’t necessarily make you a strong fit for a sales role. I want to build an elite sales team. There are many faithful, wonderful Christians who are not a good fit for sales. Convince me that you are not one of them.
Conclusion
Working at Hallow is amazing. If you’re interested, apply. The best way to discern if something is for you is to take a shot at it. If you don’t apply, please don’t ask any employee to take the time to learn about the company. I know it sounds tough, but most of us really do work about 1.5 jobs at a time to keep this going with such a small team.
If you don’t want to take the time to fill out the application, we probably don’t want to take the time to talk you through all the things you already know about the company. I, however, am not the official spokesperson for all employees. And yet, I’ve never really found anyone who feels differently about this.
Apply! Give it a go. If you’re amazing, we’d love to have you. I hope this was helpful. If you have questions, leave them in the comments!
God bless you on your career journey. And please, pray for us!


