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Sep 5, 2016 · 22m · top-founders

Cirrius Insights $640K MRR 100,000 Customers

Brandon Bruce · 13m spoken Nathan Latka · 6m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Host Nathan Latka interviews Brandon Bruce, co-founder and COO of Cirrus Insight, exploring how the bootstrapped Salesforce integration platform scaled to $640,000 in monthly recurring revenue, 100,000 users, and net negative churn through lean capital efficiency and inbox-native product innovation.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 32.2% of the talking time here. How this is scored →

Nathan as informed peer 5.4 Guest teaching 2.2 Guest disagreement 1.2 Nathan pushing back 2.6
05100:0010:0020:002:41–6:42 · Nathan as informed peer 5/10 Salesforce AppExchange Strategy, User Scale, and Monthly Revenue Nathan attempts to calculate Cirrus Insight's MRR by multiplying total user count by retail seat price. Brandon politely corrects the methodology by explaining legacy pricing and enterprise volume discounting.6:42–11:40 · Nathan as informed peer 6/10 Competitive Positioning, Net Negative Churn, and Unit Economics Nathan showcases strong SaaS domain familiarity by defining net negative churn accurately and verifying unit economics with Brandon, who fully agrees.11:40–15:38 · Nathan as informed peer 6/10 Bootstrapping Philosophy, Financial Discipline, and Growth Targets Nathan demonstrates financial fluency by instantly converting Brandon's projected $15M-$20M annual run rate target into monthly MRR equivalents.15:38–17:46 · Nathan as informed peer 6/10 Product Expansion and Inside Sales Organization Architecture Nathan cites predictable revenue architecture and breaks down AE quota targets into annual bookings versus new MRR additions.17:46–22:27 · Nathan as informed peer 4/10 Rapid-Fire Finale, Acquisition Speculation, and Concluding Thoughts Nathan probes aggressively on exit multiples and whether Brandon would sell to Salesforce for $150M, prompting Brandon to diplomatically sidestep naming a hard number.2:41–6:42 · Guest teaching 4/10 Salesforce AppExchange Strategy, User Scale, and Monthly Revenue Nathan attempts to calculate Cirrus Insight's MRR by multiplying total user count by retail seat price. Brandon politely corrects the methodology by explaining legacy pricing and enterprise volume discounting.6:42–11:40 · Guest teaching 2/10 Competitive Positioning, Net Negative Churn, and Unit Economics Nathan showcases strong SaaS domain familiarity by defining net negative churn accurately and verifying unit economics with Brandon, who fully agrees.11:40–15:38 · Guest teaching 1/10 Bootstrapping Philosophy, Financial Discipline, and Growth Targets Nathan demonstrates financial fluency by instantly converting Brandon's projected $15M-$20M annual run rate target into monthly MRR equivalents.15:38–17:46 · Guest teaching 1/10 Product Expansion and Inside Sales Organization Architecture Nathan cites predictable revenue architecture and breaks down AE quota targets into annual bookings versus new MRR additions.17:46–22:27 · Guest teaching 3/10 Rapid-Fire Finale, Acquisition Speculation, and Concluding Thoughts Nathan probes aggressively on exit multiples and whether Brandon would sell to Salesforce for $150M, prompting Brandon to diplomatically sidestep naming a hard number.2:41–6:42 · Guest disagreement 1/10 Salesforce AppExchange Strategy, User Scale, and Monthly Revenue Nathan attempts to calculate Cirrus Insight's MRR by multiplying total user count by retail seat price. Brandon politely corrects the methodology by explaining legacy pricing and enterprise volume discounting.6:42–11:40 · Guest disagreement 1/10 Competitive Positioning, Net Negative Churn, and Unit Economics Nathan showcases strong SaaS domain familiarity by defining net negative churn accurately and verifying unit economics with Brandon, who fully agrees.11:40–15:38 · Guest disagreement 1/10 Bootstrapping Philosophy, Financial Discipline, and Growth Targets Nathan demonstrates financial fluency by instantly converting Brandon's projected $15M-$20M annual run rate target into monthly MRR equivalents.15:38–17:46 · Guest disagreement 1/10 Product Expansion and Inside Sales Organization Architecture Nathan cites predictable revenue architecture and breaks down AE quota targets into annual bookings versus new MRR additions.17:46–22:27 · Guest disagreement 2/10 Rapid-Fire Finale, Acquisition Speculation, and Concluding Thoughts Nathan probes aggressively on exit multiples and whether Brandon would sell to Salesforce for $150M, prompting Brandon to diplomatically sidestep naming a hard number.2:41–6:42 · Nathan pushing back 3/10 Salesforce AppExchange Strategy, User Scale, and Monthly Revenue Nathan attempts to calculate Cirrus Insight's MRR by multiplying total user count by retail seat price. Brandon politely corrects the methodology by explaining legacy pricing and enterprise volume discounting.6:42–11:40 · Nathan pushing back 2/10 Competitive Positioning, Net Negative Churn, and Unit Economics Nathan showcases strong SaaS domain familiarity by defining net negative churn accurately and verifying unit economics with Brandon, who fully agrees.11:40–15:38 · Nathan pushing back 2/10 Bootstrapping Philosophy, Financial Discipline, and Growth Targets Nathan demonstrates financial fluency by instantly converting Brandon's projected $15M-$20M annual run rate target into monthly MRR equivalents.15:38–17:46 · Nathan pushing back 2/10 Product Expansion and Inside Sales Organization Architecture Nathan cites predictable revenue architecture and breaks down AE quota targets into annual bookings versus new MRR additions.17:46–22:27 · Nathan pushing back 4/10 Rapid-Fire Finale, Acquisition Speculation, and Concluding Thoughts Nathan probes aggressively on exit multiples and whether Brandon would sell to Salesforce for $150M, prompting Brandon to diplomatically sidestep naming a hard number.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 39.5% · guest 60.5%0:00 · Nathan 39.5% · guest 60.5%3:00 · Nathan 24.7% · guest 75.3%3:00 · Nathan 24.7% · guest 75.3%6:00 · Nathan 28.8% · guest 71.2%6:00 · Nathan 28.8% · guest 71.2%9:00 · Nathan 25.9% · guest 74.1%9:00 · Nathan 25.9% · guest 74.1%12:00 · Nathan 28.4% · guest 71.6%12:00 · Nathan 28.4% · guest 71.6%15:00 · Nathan 39.5% · guest 60.5%15:00 · Nathan 39.5% · guest 60.5%18:00 · Nathan 32.1% · guest 67.9%18:00 · Nathan 32.1% · guest 67.9%21:00 · Nathan 46.8% · guest 53.2%21:00 · Nathan 46.8% · guest 53.2%
Sharpest disagreement ▶ 21:26 Brandon deflects acquisition floor price

When Nathan presses Brandon on the minimum acquisition multiple and whether $150M from Salesforce is enough, Brandon pushes back on giving a hard number and emphasizes market-driven valuations.

 Hardest push from Nathan ▶ 5:49 Nathan rejects ARPU ambiguity

Nathan cuts past fluctuating seat pricing to demand the exact January 2016 MRR figure rather than accepting high-level seat estimations.

 Biggest teaching moment ▶ 19:09 Assistant.to acquisition reveal

When Nathan asks whether Brandon is considering buying Assistant.to as a competing tool, Brandon surprises him by explaining they already acquired and integrated the company nine months prior.

 Nathan holds their own ▶ 8:32 Nathan explains net negative churn

Nathan steps in to give a precise textbook breakdown of net negative churn to educate the audience, prompting Brandon to affirm the explanation completely.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Salesforce AppExchange Strategy, User Scale, and Monthly Revenue 5413 Nathan attempts to calculate Cirrus Insight's MRR by multiplying total user count by retail seat price. Brandon politely corrects the methodology by explaining legacy pricing and enterprise volume discounting.
Competitive Positioning, Net Negative Churn, and Unit Economics 6212 Nathan showcases strong SaaS domain familiarity by defining net negative churn accurately and verifying unit economics with Brandon, who fully agrees.
Bootstrapping Philosophy, Financial Discipline, and Growth Targets 6112 Nathan demonstrates financial fluency by instantly converting Brandon's projected $15M-$20M annual run rate target into monthly MRR equivalents.
Product Expansion and Inside Sales Organization Architecture 6112 Nathan cites predictable revenue architecture and breaks down AE quota targets into annual bookings versus new MRR additions.
Rapid-Fire Finale, Acquisition Speculation, and Concluding Thoughts 4324 Nathan probes aggressively on exit multiples and whether Brandon would sell to Salesforce for $150M, prompting Brandon to diplomatically sidestep naming a hard number.

Statements from this episode (12)

Assertion Partly supported
Cirrus Insight launched the first Salesforce-Gmail integration in 2011
“In 2011, launched the first integration of Salesforce, which is the famous customer relationship management platform in the cloud, and Gmail.”
Brandon Bruce Sep 5, 2016 ▶ 1:28
Assertion Not checkable as stated
Cirrus Insight serves 100,000 end users across 3,500 organizations
“Yeah, we serve about a 100,000 end users and those are spread across over 3500 organizations.”
Brandon Bruce Sep 5, 2016 ▶ 4:53
Disclosure
Cirrus Insight charges $19 per user monthly, billed annually
“So today it's 19 dollars a user a month paid annually. And then we just introduced a new plan, a closer plan about six weeks ago that includes some additional functionality, like the ability to mass email out to customers and some higher end calendar integrati…”
Brandon Bruce Sep 5, 2016 ▶ 5:35
Assertion Not checkable as stated
Cirrus Insight finished 2015 with approximately $640,000 in MRR
“So the, so MRR, we finished 2015 at around six 40 K.”
Brandon Bruce Sep 5, 2016 ▶ 6:31
Assertion Not checkable as stated
Bruce: Cirrus Insight maintains net negative churn
“So net negative turn. So we always add more seats then we lose”
Brandon Bruce Sep 5, 2016 ▶ 7:59
Assertion Not checkable as stated
Cirrus Insight maintains a $750-$800 LTV against an $85 CAC
“So our LTV right now is between 758 hundred dollars. You know, cost of customer acquisition is about 85 bucks. So, you know, we're able to recover our CIC pretty fast.”
Brandon Bruce Sep 5, 2016 ▶ 9:58
Assertion Not checkable as stated
Cirrus Insight has over 350 consulting partners and resellers
“So we have a network of over 350 consulting partners as well as some resellers.”
Brandon Bruce Sep 5, 2016 ▶ 10:41
Disclosure
Cirrus Insight raised approximately $1.15M total via convertible notes
“About 1.15 million or so.”
Brandon Bruce Sep 5, 2016 ▶ 12:23
Disclosure
Cirrus Insight operates at break-even to reinvest in growth
“Yeah, we basically try to keep it at break even. That's essentially our goal. So we reinvest everything in growth of the company.”
Brandon Bruce Sep 5, 2016 ▶ 13:13
Assertion Not checkable as stated
Outlook represents 75% of the market with 4-5x larger customers
“And then we're really ramping into this outlook market, which, you know, by most estimates is about 75% of the market and those customers are four or five times larger.”
Brandon Bruce Sep 5, 2016 ▶ 15:05
Disclosure
Cirrus Insight targets a $50K monthly quota per account executive
“On the quota side, we're aiming on average. So it varies based on tier, but on average about 50 K a month. Per, per, per account executive.”
Brandon Bruce Sep 5, 2016 ▶ 17:01
Assertion Supported
Cirrus Insight acquired scheduling tool Assistant.to
“We've acquired them already about nine months ago. We added the functionality in the Sears Insight. It's one of our most popular features.”
Brandon Bruce Sep 5, 2016 ▶ 19:17
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