They say that time is money, so saving time is the same as saving money. One startup that’s trying to do
just that for its clients is LeasePilot, which helps commercial real estate companies to draft their leases
in half of the time it currently takes.
Operating at the cross-section of commercial real estate and lawyers has given LeasePilot a unique
perspective on what it takes to find success in the startup world, even with co-founder Gabriel Safar being
a former lawyer. Gabriel joined startup coach Roland Siebelink on the latest episode of the Midstage Startup
Momentum Podcast on LeasePilot’s journey and what he’s learned along the way.
- Why great technology is only part of the equation in finding success.
- The biggest challenge LeasePilot has faced as a B2B startup.
- Operating a business that has multiple stakeholders with different interests.
- Why LeasePilot is trying a direct approach on its go-to-market.
- The steps LeasePilot took to determine the best potential customers to target.
- Why LeasePilot’s metrics relate to the value they provide.
Roland Siebelink:Hello and welcome to the Midstage Startup Momentum
Podcast. My name is Roland Siebelink and I'm the founder and CEO of the Midstage
Institute. We help fast-growing startups scale even better. And in our podcast,
we invite some of the world's most renowned founders of new and fast-growing
startups to share all their learnings with other founders. Today, so proud to
have Gabriel Safar here with us, the co-founder of LeasePilot, calling in from
Boston. Hello, Gabriel. Welcome.
Gabriel Safar:Hi, Roland. Thank you very much for having me. It's a
pleasure and an honor.
Roland Siebelink:Oh, it's absolutely an honor on our side. We had so much
trouble finding a little bit of time in your busy schedule, but I'm glad it
worked out, Gabriel.
For those who don't know LeasePilot, let's just start with the basics. What do
you do? What do you offer to whom? And what difference do you make in the world?
Gabriel Safar:LeasePilot's customers are office retail and industrial real
estate organizations, commercial real estate companies. And what we do is help
them draft their leases faster. That might not sound off the bat super
impactful, but a couple of things just to keep in mind. On average, it takes
anywhere between 75 to 90 days to go from an agreed upon set of business terms
to a signed piece of paper. And that's a huge amount of friction in one of the
largest set of asset classes in the world.
And what that means is you have a lot of really smart, capable people spending a
ton of time banging their heads against the wall. And our job is to help them
redirect that time to the most productive things that they could be doing, so
that they can create value instead of process paper.
Roland Siebelink:That's excellent. And a great value proposition that I'm
sure would be very attractive to all those people with banged in heads.
Talk a little bit about how you got to that idea. Did you have a background in
that field? What was the crucial insight that led you to want to start
Gabriel Safar:That's a great question. Yes, I have a background in the
area. I'm a real estate lawyer, so I spent the bulk of my professional life
drafting leases. And I came to LeasePilot because I was able - relatively early
in my career as a lawyer - to start developing a business of my own. And I was
able to hire through my firm a career coach. And that career coach and business
development coach was really, forward-looking, a gentleman named Stuart Hirsch.
And what he tried to do in his coaching was to say, "Let's just not look at how
you get business tomorrow. Let's think about what type of impact do you want to
have on the world? What type of career do you want to have? Who you want to
And in doing that, he recommended I read a couple books. Two of the books were
hugely impactful. One was The Innovator's dilemma by Clayton Christensen, who
actually became an investor in LeasePilot. And then the other book was
Tomorrow's Lawyer by a thinker out of London at Oxford, Richard Susskind. And
thinking about the ways that lawyers are often so narrowly focused on a specific
set of agreements and looking at a document as a work product and not thinking
about how that work product serves a larger set of needs. And thinking
holistically, it opens up your mind to a lot of opportunities. And that's really
where LeasePilot came from.
Something about LeasePilot, the way that we look at the world and what makes us
innovative is we look at a document itself as a technology. And it's a very old
technology. And what the document does is it's a mechanism for capturing,
storing, and sharing information about contracts. From our perspective, the
documents served the world really well. But in a digital age, the document's an
anachronism because it's fundamentally analog.
Even if you take a Word document - at the end of the day, a Word document is a
document. You have letters strung together to make up sentences or words and
sentences, paragraphs, etcetera. And that doesn't play nice with digital
infrastructure. At LeasePilot, what we want to do is we want to swap out the
document as that fundamental technology powering agreements and transactional
relationships, and we want to replace it with a database. Now that sounds pretty
easy. It's not. And the reason it's not is because there are certain things that
the document does really well that databases don't. And that's communicating
nuance and being flexible. That's something that's super important when you have
complex commercial agreements that get enforced in court.
What we've been able to do at LeasePilot is we've been able to create what we
call the illusion of documents, where people feel like they can manipulate the
text of an agreement as if it were a document, but everything's getting tied
back to a database. The reason we're able to do that is because we've leveraged
the inherent underlying structure of certain agreements, and then we can build
on that structure and tie back that nuance to the database structure. And that
allows us to offer both the efficiency and power of a database with the
flexibility of a document.
Roland Siebelink:You mentioned as a key benchmark in the beginning that
without your technology typically it takes between 75 and 90 days between a
general agreement to actually having an agreement on paper. How far can you
reduce that with your technology and products?
Gabriel Safar:We've seen that come down in half. The reason for that is
largely because we're able to release bottlenecks. And there's two ways that our
customers think about time and that we think about time. There's the absolute
amount of time, which is something that took me three hours or should take me
one hour. And we can see at LeasePilot - we take a lot of surveying of our
customers - something that took three hours should now take anywhere between an
hour to an hour and a half. We're saving more than 50% of the absolute time.
Roland Siebelink:That sounds very, very cool and a very attractive product
if you're in that business. Let's talk about your go-to market. Who do you
target? How do you reach them? How do you convince them? How difficult is the
sales cycle and so forth?
Roland Siebelink:Why is that? Does it have anything to do with what you
said about lawyers being conservative by any chance?
Gabriel Safar:Not necessarily. I think lawyers are people - going out on a
limb here, they're people.
Roland Siebelink:I'm trying not to respond, but as a European, I don't
necessarily always have the bad image of lawyers in my head that the typical
Gabriel Safar:I have a great image of lawyers because I'm one. I understand
how hard their job is. And I think often people don't come at what lawyers do
with enough empathy. On the one hand, they feel like, "Oh, this stuff should
just be done immediately." And on the other hand, when something goes wrong,
who's the one who's having the rifle pointed at them? It's the lawyer.
Business people talk out of both sides of their mouth when they say, "I wish the
lawyers didn't make everything complicated." But the second something goes
wrong, we're going to pillory them. You can't have your cake and eat it too.
Roland Siebelink:Some people just don't want to accept that the world
itself is a complex place, right?
Gabriel Safar:Well, the world is a complex place. These agreements are
inherently complicated, and people aren't willing to tolerate - they're pretty
risk averse - and they hire lawyers to have that risk averse function. That's
what they do. And that serves a very important function. I think the reason
lawyers tend to bristle at a lot of technology is because most of the technology
doesn't come at them with any understanding of what they do. And it doesn't come
from a position of empathy. It's engineers who are designing something that
sounds cool. And they're like, “Why can't you turn this contractual relationship
into a set of Mad Libs?" Lawyers, just use it and shut up. And the world just
doesn't work that way. When you come at the legal profession with a set of
empathy and trying to understand how hard their job is, they're willing
What I underestimated as a founder and as an entrepreneur is that ultimately the
technology's a super small part of what you're doing. It's understanding people
and their incentives and the change management that you need to be able to
provide for. That's a massive, massive piece of being successful. And it's so
easy to underestimate. What I find challenging about a B2B sale -and especially
in the type of sale that we're doing - is you have multiple stakeholders with
very different interests. Managing and understanding those interests takes time.
And it takes a lot of understanding of your customers. That's one of the things - at
least, on my journey as an entrepreneur - I'm trying to get a better hold
of so that we can sell with less friction.
Roland Siebelink:Okay. Excellent. What would you say is your ideal customer
profile? Is it individual lawyers? Small firms? Large firms? How else do you
distinguish your ideal customers from your not so ideal customers?
Gabriel Safar:We don't sell to any law firms right now. Our users are the
real estate owners, who are our customers. The reason for that is, they're the
ones that benefit from the time-savings. Our users are lawyers, both the
internal lawyers at the real estate organization, if they have them, or the
outside lawyers working off of a license for our customers.
Roland Siebelink:Yes, exactly. Because in the traditional law firm model, a
reduction in time would only be against the incentives of the lawyer's billing
Gabriel Safar:It depends. That's the simplistic view. And it's often the
view that many people have. If you think about the profitability of an
organization, that might actually not necessarily be true. One of the things
that I thought about when I was a lawyer is how well am I getting paid? What am
I able to collect on my bills? As customers are really looking for value, and
real estate customers and any commercial customers looking at business
arrangements, they're savvy, and they don't want to pay for lawyers that aren't
providing value. If you think about it from the perspective that we can help a
law firm increase that ratio of value to unit of billing, you can actually help
them be more profitable. That said, we still sell to the real estate companies
because making that nuanced argument is just painful with law firms.
Roland Siebelink:I can see that. Basically, you sell to the actual users,
the real estate companies. What's your go-to market there? Do you have an ICP in
mind? Do you have specific tactics in order to reach them? Do you use an
existing network? How do you go about that go-to market? I'm only asking because
I know that's always the question on the mind of all the listeners to this
podcast. How do you actually design a go-to market for the product?
Gabriel Safar:Yeah, we're experimenting right now. What we've been doing is
we've had a very direct go-to market. And I've experimented with a lot of
different go-to market strategies. Early on, I just loved the idea of inbound
marketing. And I thought, "Oh, we put out content and you do all of these
magnets and people come to you and then they just sign up for the product." I
realized that that was incredibly naive. I think it can work at scale, but
making a content-based marketing strategy where people come to you and they're
truly qualified and you're not wasting your time following up on irrelevant,
inbound leads requires a lot of investment in the way that you do your
marketing, the team, the content delivery. It's a heavy lift.
What we've found extremely effective, which shocked me, is just calling people.
And the cold call has been so effective. And what I learned about cold calling -
which I did a lot of them myself - was you cut to the chase and you lead with a
question that's on people's mind. What drives me batty to no end is when you get
these cold emails that say, "Will you meet with me?" No, I'm not going to meet
with you when you ask me that. If you start with something - what we use is
"Fast and responsive leasing." It's almost like "Fast and responsive leasing,
that's almost an oxymoron." And it's something that our customers are thinking
about because they're feeling like their leasing is slow and unresponsive. That
gets someone's attention.
Roland Siebelink:Very good. And sometimes it's good to hear that some of
the old techniques still work better. It does require you to have a pretty good
idea of who is on your target list if you do any cold outreach. How did you
reduce the universe to those companies where you feel like you'll have the
biggest chance of success? Is that still part of the experiment or do you have a
pretty good idea who to target at this stage?
Gabriel Safar:We have a very good idea who to target at this stage and we
invested quite a bit in that. And I think that's right in that reaching out to
the right people is key because your conversion ratio will be zero if you're
calling the wrong people. What we did was we invested quite a bit in building a
list. We were not able to buy a list from anywhere, but we tried many times.
What we did was we built it company by company, by reading trade magazines, by
scraping databases, by all sorts of different mechanisms.
And then what we did was we would put companies - we use HubSpot as our CRM - we
put a large set of companies into HubSpot. And then we needed to think about
what makes a customer a good customer for LeasePilot? And ultimately, it's about
leasing and leasing activity. You can't find that. There's nowhere where you can
go and ask, "Tell me how many leases a given company can have." And it's very
hard to find a clear direct relationship between any one attribute. You can have
really big companies that own a lot of square footage, but have really big
leases and they don't do many of them. We had to look at taking a combination of
the number of buildings, size, type of ownership structure. And we built a model
with five attributes that we thought would contribute to making a customer good
or not good.
And then what we did is we said each one of those attributes needs to be
knowable by searching three sources: their website, ZoomInfo, or LinkedIn.
That's it. No telephone calls, nothing that's secret. And we call that a fit
score. And then we paid a resource, a contractor, to go and just do that
research. We'd say here's the hundred companies for you to research. And then we
made a very structured process where the researcher would research and they
would hit a certain stage in the research where they would say, "Here's a fit
score." Then I would review that fit score and I might reject it because they
would get things wrong. And it took a lot of learning. We'd go back and forth
and then hit the stage where we would say that it's hit a stage where this
company has been sufficiently vetted that it's okay to add contacts to it.
And then we identified who our key personas were and who we wanted to sell to.
For each one of those companies, we added three to five contacts. Our focus is
on qualifying an account, and that's super important. But you can't speak to an
account. You have to talk to human beings. You have to talk to people and
contacts. And so, we identified who were our core contacts that we wanted to
talk to. Then those went into the database after we pre-qualified an account.
Roland Siebelink:You talked in the beginning, Gabriel, about the different
stakeholders that you have to navigate in B2B sales. I'm assuming those maps to
the personas that you are looking to contact, did you find a specific role in
the company that's almost always your best entry point and then some other
stakeholders come in later in the process? Or do you try to get in through any
stakeholder and just see where it lands first?
Gabriel Safar:The first answer is it's not always the same stakeholder. But
the second answer is we don't just try to reach anyone and get in. We've
narrowed it down to a series of three to four stakeholders that matter. We will
look at those different stakeholders and we have different sets of email
campaigns and cold call scripts for each one of those stakeholders that are
specific to them.
Roland Siebelink:Excellent. Okay. Very good. Do you do those in parallel
typically or more, we tried this one first and then if that didn't work, we try
to campaign on the next stakeholder?
Gabriel Safar:I'm too impatient to do things sequentially.
I do them all at the same time. And I've had people say, "Is that good?" You
know what, if I get an email and a colleague of mine gets an email and we share
the email, we're talking about that company; that's a good thing. It doesn't
bother me if I send four emails to a company. I don't even care if it's the same
email if they have the same role. What I care about is, is that message clear
and is it something that the reader or the recipient it's on their mind. And I
find marketing people aren't good at that. They put too much marketing, gobbly
goop that they find in some thesaurus rather than putting themselves in the
shoes of the person who is the recipient of the information and asking them "Do
I care." In that way you meet them where they are.
Roland Siebelink:Yeah, exactly. I love that. Very good. Can you talk a
little bit about some indicators around traction at LeasePilot? Where are you
at? How far have you grown? How do you see yourself having success in the
Gabriel Safar:The thing that we watch most obsessively - actually, there's
a couple things that we look at really obsessively. What indicates traction from
our perspective is the number of transactions or leases that are handled on our
platform. Just to provide a bit of context, last year we processed around 1,600
leases on LeasePilot's platform. This year, we're expecting to do around 3,500
leases on LeasePilot.
Roland Siebelink:Okay. That's more than doubling up. That's great. Very
cool. What other metrics - you said you have a few metrics that you watch
obsessively - what are some of the others that you also have?
Gabriel Safar:Our approach to metrics is really about starting - I'd say
subjectively - we try to figure out what do we want to understand? What do we
want to learn? And then we work back to build KPIs. One of the things that we
really want to understand is, are we creating value for our customers. We define
value in terms of speed. We have an in-app survey, which is asking our customers
how much time did you actually save? We obsess over that and we're seeing that
it's between 75 to 50%. With some of our older customers that aren't able to
answer any more because they don't remember what it was like to actually prepare
a lease without LeasePilot.
Roland Siebelink:Amazing story, Gabriel. Really appreciate this. If people
want to hear more about LeasePilot, where should they go and what could they
help you with?
Gabriel Safar:Great questions. Thank you for asking that. Where they can go
is to our website, which is LeasePilot.co. No com, just dot CO. And what they
could help us with is - we're looking to engage with thoughtful, smart people
that really want to change the way that lawyers interact with documents and
forms and to help them think about creating more value for their end customers.
We welcome those conversations. We're thrilled to have been invited to
participate in the World Economic Forum. We're a group of one of the hundred
global innovators. Thoughts matter and conversations matter.
Roland Siebelink:Yeah. Very cool. Excellent. People, visit LeasePilot.Co,
not com, and you will find everything there is to know about LeasePilot. Is
there anything you want them to download or look at, in particular?
Gabriel Safar:Yeah, we have a full demo on our website that's a video.
Check out the demo. One of our philosophies is to be super transparent, so we
don't hide the ball. Everything's right there up on the web.
Roland Siebelink:Excellent. Okay. Gabriel Safar, thank you so much for your
time. The co-founder of LeasePilot, calling in from Boston. It's been an honor
having you on the podcast and I appreciated your key insight into how to build a
go-to market. I think a lot of founders will love it too.
Gabriel Safar:Thank you very much, Roland. I appreciate you inviting me.
Roland Siebelink:Absolutely. Thank you, listeners. And we'll have a new
episode for you next week. Bye-bye.
Roland Siebelink talks all things tech startup and bring you interviews with tech cofounders across the