Ian Crosby Profile Banner
Ian Crosby Profile
Ian Crosby

@ianwcrosby

Followers
2,157
Following
69
Media
37
Statuses
1,169

Let’s build great things and win. Head of Accounting Products @mercury . Fmr CEO and Co-founder of and . Ex-Shopify.

Vancouver, Canada 🇨🇦
Joined August 2011
Don't wanna be here? Send us removal request.
Explore trending content on Musk Viewer
@ianwcrosby
Ian Crosby
4 years
@whileonefork I’m an EWOK type, I don’t get along with ATST but I love JEDI. Anyone who laughs at this tweet is a NERD.
1
1
271
@ianwcrosby
Ian Crosby
3 years
I'm excited to share that I've joined @Shopify to lead Product for Balance! I'm looking forward to making Balance not just a massively successful product, but a very special one in the lives of our merchants. We're hiring UX/Product/Eng - DM me!
20
9
270
@ianwcrosby
Ian Crosby
5 years
I've been using this card and everything about the UX is absurdly better than any other corporate card I've ever used. Thank you @patrickc , @cjc , and the entire @stripe team for making this card a reality. We're excited to bring it to @Bench 's clients.
4
11
197
@ianwcrosby
Ian Crosby
25 days
Today I'm excited to announce that Teal has been acquired by @mercury ! We're very excited to make banking and accounting seamless for accountants and entrepreneurs.
@immad
immad
25 days
Excited to make our first acquisition and make great things with @ianwcrosby and team!
22
2
209
20
8
175
@ianwcrosby
Ian Crosby
3 years
Two huge announcements @Bench ! 1. Today, Bench re-launches as an all-in-one financial platform with banking, bookkeeping, taxes, and advice, all designed to work together beautifully. 2. Bench has raised a $60M Series C from Contour, Altos, iNovia, BMO T&I, Sage, and Shopify.
@globebusiness
Report on Business
3 years
Shopify invests in Vancouver’s Bench Accounting
0
3
9
19
13
161
@ianwcrosby
Ian Crosby
4 years
I’m a @LambdaSchool contrarian. I think it’s going to be way bigger than even you @Austen realize right now. It is so rare in life to be able to make a real difference in one person’s quality of life. @LambdaSchool is mass producing changed lives. This tweet is on track:
@ianwcrosby
Ian Crosby
6 years
People are going to wake up one morning in about 10 years and realize @AustenAllred and @LambdaSchool have solved education, eradicated student debt, reversed growing inequality, and ultimately saved liberal democracy.
1
7
72
4
9
110
@ianwcrosby
Ian Crosby
6 years
I just came across @LambdaSchool . Holy crap. This is the future of education.
4
5
87
@ianwcrosby
Ian Crosby
6 years
People are going to wake up one morning in about 10 years and realize @AustenAllred and @LambdaSchool have solved education, eradicated student debt, reversed growing inequality, and ultimately saved liberal democracy.
1
7
72
@ianwcrosby
Ian Crosby
10 years
Manager's guide to success: 1. Hire smart people. 2. Give them the right tools. 3. Get out of the way.
3
36
55
@ianwcrosby
Ian Crosby
4 months
It's been an incredible year working again with my close friend @adamjsaint to launch our 2nd startup, Teal. Today we're announcing our $8M seed round led by Katie Reiner at @torch , with participation from General Advance, @BasisSet and Dash Fund. With a first set of incredible
@BetaKit
BetaKit
4 months
. @Bench and @Shopify alumni announce $11 million CAD to build “the Stripe for accounting” with Teal. #YVRtech #CDNtech
0
0
3
9
3
46
@ianwcrosby
Ian Crosby
6 years
Good management is brilliant people looking at high quality data and having honest conversations. Bad management is ethically flexible people manipulating arbitrary data to push an agenda. If you find the former, join the team and hang on tight. They are rare and powerful.
1
26
43
@ianwcrosby
Ian Crosby
8 years
. @intuit I will take the fact that you advertise using our photography from @Unsplash as a compliment!
0
13
38
@ianwcrosby
Ian Crosby
3 years
@Samirkaji I’m on the opposite end of the spectrum. I ignore scripted behaviours and look only for whether they will (1) care about the mission, (2) do a good job and (3) be great to work with. Teammates don’t send me thank you emails after meetings so candidates don’t need to either!
1
0
34
@ianwcrosby
Ian Crosby
6 years
When I was in business school, Porter's 5 Forces was held up as the epitome of business strategy. A decade into my career, it's painful obvious that's wrong. The real 5 forces are: 1. Culture. 2. Culture. 3. Culture. 4. Culture, and 5. Luck.
3
4
30
@ianwcrosby
Ian Crosby
8 years
I thought my daughter was playing games on the iPad this morning, but it turned out she was checking her P&L.
0
4
22
@ianwcrosby
Ian Crosby
9 years
Thanks to @StevenBertoni & others @Forbes for this. It’s an honour #30Under30
4
4
23
@ianwcrosby
Ian Crosby
6 years
My business goals have been so chickenshit. My new customer survey question is going to be “Have we made a profound difference in your quality of life?” Then I’m going to build like hell until my team has gotten “yes” from a million people. #GoBig
1
2
22
@ianwcrosby
Ian Crosby
9 years
In absence of good data, most people will create strongly held beliefs based on unrepresentative anecdotes and wishful thinking.
3
8
16
@ianwcrosby
Ian Crosby
2 years
Spent some time working with @adamjsaint today on a new startup. I forgot how great it was to work with highly competent friends. Such a joy.
4
0
19
@ianwcrosby
Ian Crosby
1 year
It’s pretty clear at this point that has hit on something big. If you want to join a team of competent people focussed on winning, we’re hiring our first PM role:
4
3
17
@ianwcrosby
Ian Crosby
6 months
Justin Trudeau thinks he can allocate capital better than entrepreneurs.
3
0
17
@ianwcrosby
Ian Crosby
5 years
We’re hiring over 200 people. But before people join @Bench , I wanted to share an unvarnished view of what it's really like. It's hard and messy. But incredibly worthwhile. Thank you @DailyHiveVan and @darcynews for the honest story.
0
1
16
@ianwcrosby
Ian Crosby
4 years
2
0
14
@ianwcrosby
Ian Crosby
4 years
When I was growing up, my family constantly warned me that starting a business was “risky.” “Look at your great uncle, he lost his shirt in business. Far better to study a profession.” Why do we reflexively feel that sending an invoice is riskier than $100k in student debt?
2
2
16
@ianwcrosby
Ian Crosby
9 years
2006: Yahoo offers $1B to buy Facebook. 2016: Facebook offers $1B to buy Yahoo.
0
7
16
@ianwcrosby
Ian Crosby
5 years
Big day at @Bench today, we just released a massive expansion to our service: Pulse. From today, all Bench customers now have a real-time view of cash in and cash out, across all their cards and institutions.
0
2
15
@ianwcrosby
Ian Crosby
6 years
Hey #Vancouver @bench is growing and we’re hiring 100+ people by Christmas. Everything from engineering to account support, entry-level to senior. Come look at what we’ve got!
0
4
14
@ianwcrosby
Ian Crosby
8 years
Welcome cards for me to sign for our new March customers. The tiny monthly stack has grown!
Tweet media one
0
0
14
@ianwcrosby
Ian Crosby
4 years
Signatures are an anachronistic, insecure way to “verify“ identity in 2020. Moving to e-signatures feels like “well we have no idea why we’re doing this but let’s at least do it online.”
3
1
14
@ianwcrosby
Ian Crosby
5 years
So I just got a frivolous email from @Intuit 's legal department. Sorry guys, @Bench won't be intimidated.
1
0
14
@ianwcrosby
Ian Crosby
7 years
Thanks @hainsworthtv for having me on the show today! We're excited to solve bookkeeping for Canadian small businesses! @bench @BNN
0
3
14
@ianwcrosby
Ian Crosby
6 years
We just lowered our lowest price from $115/mo to $95/mo. Medium-term plan is to price in the $40-60/mo range and pack the entry package with even more service and value. Goal is to be *ridiculously* valuable to entrepreneurs.
1
2
13
@ianwcrosby
Ian Crosby
4 years
@awilkinson h o w a b o u t a q u i c k c a l l
0
0
13
@ianwcrosby
Ian Crosby
9 years
Could Homer use your app? That's a good test of intuitiveness. http://t.co/Uzg5HxpcZK
Tweet media one
0
6
11
@ianwcrosby
Ian Crosby
8 months
Here's what people don't understand about vertical saas. Shopify, Toast, Service Titan - they are each just getting started. And there are still so, so many untouched verticals. We need 100x more Shopify's. 99.99% of vertical saas market cap is yet to be created.
2
1
10
@ianwcrosby
Ian Crosby
3 years
I used to have to go skydiving to have the experience of plummeting to Earth. Now I just need to hold bitcoin.
1
0
12
@ianwcrosby
Ian Crosby
4 years
@cjc Shape Up > Agile
0
0
12
@ianwcrosby
Ian Crosby
7 years
"It has saved me, it has saved my business and my sanity, and heaven forbid, my marriage" - @fbombchic and @KevinPricePOB , I'm so humbled that @Bench could have this effect on your life and I wish you the best with your business!
0
1
11
@ianwcrosby
Ian Crosby
5 years
Fintechs like @Bench @Square and @Plaid are standing by to help quickly and at massive scale. @stevenmnuchin1 @USTreasury you don't need to rely on intransigent banks. We are ready to help *today*. @zachperret @jack
2
1
11
@ianwcrosby
Ian Crosby
6 years
VC: have you considered increasing customer retention by removing the “cancel” button and instead making people call into an obscure support line and torturing them for an hour? Me: 🤦🏼‍♂️
2
2
11
@ianwcrosby
Ian Crosby
3 years
Love @Calendly but would be 10x better if it went from: “Here’s some of Sarah’s open time slots, now open your own GCal in another window and reconcile some times that work for you both” To: “Login with your GCal and we’ll only propose times that work based on both calendars”
4
0
9
@ianwcrosby
Ian Crosby
9 months
Good morning to all the builders out there. This is your year to shine!
2
1
10
@ianwcrosby
Ian Crosby
6 months
@bryan_johnson You want to align us with ourselves, so we can understand how to align with AI. Did I get it?
1
0
10
@ianwcrosby
Ian Crosby
6 years
The tech conventional wisdom is to figure out how to charge your customers more. It’s what I hear every time I walk out of a VC meeting. But I want to figure out how to charge customers *less* and *give* them more.
2
0
10
@ianwcrosby
Ian Crosby
6 years
The more I lead, the more I learn that leadership isn’t what I thought it was.
1
0
10
@ianwcrosby
Ian Crosby
6 years
Are you giving your friends and family the best side of you? Or the bookkeeping side of you? We launched our latest creative campaign today here at @Bench ! Thanks to everyone in the marketing team at Bench who helped bring this one to life! #smallbusiness
1
3
9
@ianwcrosby
Ian Crosby
5 years
Staying at a hotel in SF, which has just informed me that the bill for my stay will be $NaN dollars, including $syntax error in taxes. Turns out there still a ton of opportunity in software.
Tweet media one
3
0
9
@ianwcrosby
Ian Crosby
3 years
Bad Product Management -> "What can we add?" Good Product Management -> "What can we simplify?"
0
2
9
@ianwcrosby
Ian Crosby
8 years
Today (and every day, really) I recognize all the intelligent women in my life and at Bench. Thank you ♀️
0
0
9
@ianwcrosby
Ian Crosby
8 years
Be polite. It costs you nothing, and people will appreciate it.
1
1
9
@ianwcrosby
Ian Crosby
6 years
Standing desks are so last year. I just bought a standing bed because sleeping is the new smoking.
0
0
9
@ianwcrosby
Ian Crosby
6 years
Every time I read about kids taken from their parents at the Mexican border, I imagine my own kids being taken from me, put in a facility, terrified and helpless. How can we as human beings allow this to happen on our watch?
1
0
9
@ianwcrosby
Ian Crosby
4 years
1) Most mature F500 companies are social status games that are only loosely mapped to markets. These companies persist only because of moats that keep challengers at bay. But the moat in retail banking has just been crossed, and banks are in for a shock. 🧵
2
0
9
@ianwcrosby
Ian Crosby
4 years
Business isn’t risky. Personal debt is risky. Whether it’s to finance education, personal consumption, or starting a business. Find ways to avoid personal debt and you will avoid so much anxiety and misery. There are a million ways to start in business without debt.
3
0
9
@ianwcrosby
Ian Crosby
5 years
@Austen 3 systems for quality at scale: (1) objective measures of quality at a unit level for (a) customer (b) team member (c) a unit of work. (2) a training program that doesn’t let new employees serve customers until they demonstrate hitting quality measures in (1)
1
0
9
@ianwcrosby
Ian Crosby
4 years
Now that I’m back into the product world, I’m looking forward to my assigned reading from @adamjsaint
Tweet media one
0
0
6
@ianwcrosby
Ian Crosby
6 years
Password requirements: 2005: Must contain 8+ characters 2010: Must contain an upper and lowercase letter 2015: Must contain a symbol 2020: Must contain an emoji 2025: Must contain a limerick 2030: Must contain a stargate rune 2035: Maybe the problem isn't password complexity
1
0
7
@ianwcrosby
Ian Crosby
3 years
It’s surprising to me that most companies still rely on debunked traditions in hiring / promoting / performance managing employees rather than focussing on being thoughtful and effective. Are we building for the future or the past? The best companies go their own way.
0
1
8
@ianwcrosby
Ian Crosby
9 years
Hire for ability. Not experience, education, or credentials. Those are bad proxies.
2
5
8
@ianwcrosby
Ian Crosby
5 years
Asking "What is more important to making decisions: data or intuition?" is like asking "What is more important to walking: your left or your right leg?" You are only as strong as your weakest muscle.
0
3
8
@ianwcrosby
Ian Crosby
6 years
100,000 generations of our families were lucky to live to 30. They spent their lives trying to not to starve. We tap a magic screen and food happens. What's possible for humanity now, even during our short lifetimes, is beyond imagining. Go imagine something and build it! Go!
0
0
8
@ianwcrosby
Ian Crosby
9 years
Great products aren't built by 10x engineers, they're built by 10x teams.
1
3
7
@ianwcrosby
Ian Crosby
7 years
In 2018, if it walks like a duck, and talks like a duck, it's probably BitDuck, the world's most revolutionary distributed Mallard-based block chain enabled platform for global impact.
0
1
8
@ianwcrosby
Ian Crosby
2 years
Crypto will never go mainstream so long as regular people continue having their holdings exploded by fraud. Rampant fraud will continue until there is strong and consistent regulation. The entire point of crypto is to avoid government regulation. Therefore..
1
0
8
@ianwcrosby
Ian Crosby
4 years
2020 update: Step 2) You are now a bank* *powered by @stripe
@JustJake
Jake
5 years
Startup Playbook: Step 1) Whatever you were doing before Step 2) You are now a bank
3
26
250
1
0
8
@ianwcrosby
Ian Crosby
6 years
It’s amazing what a team can accomplish when it has clear, simple, unambiguous goals. It’s amazing how little they can get done when they don’t. This is another difference between good/bad management.
0
1
8
@ianwcrosby
Ian Crosby
8 years
Engineering quality is not measured in ideological purity. It's measured in maintenance time.
0
3
6
@ianwcrosby
Ian Crosby
7 years
Honoured to be one of #CAN40under40 ! Congrats to my fellow @Top40_40 honourees @harleyf , @mkatchen , @matthswitzer
0
0
7
@ianwcrosby
Ian Crosby
8 years
Don't bother reducing the number of people that dislike your product. Just stoke the fervour of the people that love it.
1
4
7
@ianwcrosby
Ian Crosby
7 years
There's a special circle of hell reserved for people that design customer service for phone companies.
1
0
7
@ianwcrosby
Ian Crosby
4 years
Tesla market cap today: $292B Market cap of every other car manufacturer put together: $612B Tesla has grown 8x so far this year. If it grows another 2.1x it will be larger than the entire non-Tesla auto industry. 🤯
3
2
6
@ianwcrosby
Ian Crosby
4 years
Hiring by consensus leads to weak teams. Before you hire, be up-front about which *one* person makes the choice. Otherwise, you will get a weak team, and no one will be accountable for fixing it.
0
0
7
@ianwcrosby
Ian Crosby
10 years
I can't really think of any startup problem for which the solution is "go to more conferences."
0
1
7
@ianwcrosby
Ian Crosby
3 years
Come work with Satish at @Shopify and help accelerate companies like @Bench !
@skanwar
Satish Kanwar
3 years
We're growing @Shopify 's Acceleration team to work on strategic acquisitions, investments, and more. Come accelerate the future of commerce with @bram , @anna_lambert_ , @BrandonMChu , and me. 💸
11
14
244
0
0
7
@ianwcrosby
Ian Crosby
6 years
Reminds me of most “AI” startups right now.
0
0
7
@ianwcrosby
Ian Crosby
4 years
@Austen 70 years from now: But daaaaaaad, Lucy got her brain pierced when she was *12*, why can’t I?? Ugh, I’m so sick of you and this 3 dimensional reality. I’m the ONLY one of my friends not neurojamming this weekeeeeend 😭
0
0
7
@ianwcrosby
Ian Crosby
9 years
I pitched 100+ investors on Bench before anyone said yes. That's a lot of rejection. But it just takes 1.
0
3
6
@ianwcrosby
Ian Crosby
2 years
Slick card @floatcard . Nice work!
Tweet media one
1
0
7
@ianwcrosby
Ian Crosby
8 years
Too many CEOs are focussed on pleasing investors rather than building something truly great.
0
1
7
@ianwcrosby
Ian Crosby
4 years
Banking as a Service now allows a neobank to be built in 3-6 months for <$1M. The resulting proliferation of neobanks is starting to eat away at the market share of traditional banks in consumer and SMB. Banking in 10 yrs will look much different than the last 50.
2
0
7
@ianwcrosby
Ian Crosby
8 years
Imagine what we could accomplish if our institutions were optimized for producing greatness. Instead they are optimized for not looking bad.
1
0
7
@ianwcrosby
Ian Crosby
6 years
Hey @SlackHQ , I love you guys, how do I submit in-app feedback when I’m having a quality of life issue? Also, do you like Westworld? <3 @bench
1
0
7
@ianwcrosby
Ian Crosby
2 years
I'm consistently inspired by @jamesclift and the @Durableteam team. They're on to something big.
@jamesclift
James Clift
2 years
1/ I’m excited to officially launch our open beta for . Our mission is simple: remove all barriers to entrepreneurship and enable anyone to turn their skills into a profitable business. We’re also announcing that we’ve raised $6.25m.
19
18
119
0
1
7
@ianwcrosby
Ian Crosby
5 years
@Austen Hey Austen, we faced this also at Bench. Growth doesn’t cause quality to fall necessarily, that’s just conventional wisdom. Rather, there are systems you need in place to maintain quality at scale, and without them, as you approach scale at ANY speed, quality degrades.
1
0
7
@ianwcrosby
Ian Crosby
7 months
@stevekrouse I had this thought when I was 23 and here I am still shaving the damn yak 14 years later
2
0
6
@ianwcrosby
Ian Crosby
1 year
Shouting out @mintlify as an absolutely incredible platform for hosting API docs. Blown away at how this 9 person team has built the best product in the space in 18 months.
0
0
6
@ianwcrosby
Ian Crosby
1 year
We're hiring! After a productive first few months in existence and a successful fundraise, the team at is ready to add more back-end developers and dev team lead. Here's a bit more about Teal: Teal's Culture: Our mission is to build a profitable
1
1
6
@ianwcrosby
Ian Crosby
6 years
Earlier this year we fixed this and the resumes that were previously rejected had the *same* success rate in interviews. Meanwhile we *doubled* our rate of application-to-interview.
2
0
6
@ianwcrosby
Ian Crosby
3 years
Did you know that the original spelling of "fintechs" is actually "fintex" which was short for "financial total extinction" as a reference to what will happen to traditional retail banks when Stripe Treasury launches in GA? The more you know. 🤷‍♂️
0
0
6
@ianwcrosby
Ian Crosby
7 years
Hi @segment , let’s have a conversation about how to increase prices on your legacy customers, as the way you are doing it now is not okay.
2
0
6
@ianwcrosby
Ian Crosby
2 years
I'm excited to share the latest financial tool that @Shopify is adding to merchants' arsenals. Introducing the @Shopify Balance app. Here’s to Shopify redefining banking and fintech one product at a time.
1
1
6
@ianwcrosby
Ian Crosby
2 years
My close friends know that I'm passionate about dance, and have recently started taking lessons. Come see me perform live next month! On the graves of crypto prices
0
0
6
@ianwcrosby
Ian Crosby
5 years
@Austen (3) a clear chain of accountability in which managers are accountable for the quality scores of their teams and have freedom to hire / fire to achieve quality
1
0
6
@ianwcrosby
Ian Crosby
6 years
@parkerconrad @AriannaSimpson 100% agree. This seems to be a pervasive issue in tech. Big gap between what companies vs. VC's consider "helping." Most CEO's I know accept the "help" to not damage VC egos.
Tweet media one
1
1
6
@ianwcrosby
Ian Crosby
6 years
The default culture in HR is to reject resumes for petty reasons just because thats the “right” way to do HR. I guarantee your recruiters are doing this unless you’ve specifically investigated this issue.
2
1
6
@ianwcrosby
Ian Crosby
3 years
A successful Entrepreneur, one time: “Hmmm, it feels like in this one instance I should use a blue crayon.” One month later: Investors to every early stage founder: “WE ONLY FUND ENTREPRENEURS WHO USE BLUE CRAYONS”
0
0
6
@ianwcrosby
Ian Crosby
4 years
@sama Interesting, thanks for sharing! What you most agree with, and what do you most disagree with?
0
0
6