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Apr 4, 2016 · 25m · top-founders

Cirrus Insight Is Doing $640k in MRR (Dec 2015) With Much Bigger Plans EP 226

Brandon Bruce · 13m spoken Nathan Latka · 9m spoken
0:00 / 0:00

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

In this episode of 'The Top' podcast, host Nathan Latka interviews Cirrus Insight co-founder Brandon Bruce to dissect how the bootstrapped sales productivity plugin scaled to $640,000 in monthly recurring revenue and $6.5 million in ARR, detailing their customer acquisition, pricing tiers, and aggressive 2016 growth roadmap.

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 41.4% of the talking time here. How this is scored →

Nathan as informed peer 5.6 Guest teaching 2.0 Guest disagreement 0.4 Nathan pushing back 2.6
05100:0010:0020:000:59–4:52 · Nathan as informed peer 6/10 Introducing Brandon Bruce and Cirrus Insight High-Level Metrics Nathan directs the flow cleanly, asking Brandon about ARR, team size, and AppExchange ranking tactics while showing he checked the exact review counts beforehand.4:52–7:42 · Nathan as informed peer 5/10 User Metrics, Pricing Tiers, and MRR Figures Nathan attempts quick mental math multiplying 100k seats by $19 ARPU to estimate MRR, but Brandon politely corrects him by pointing out historical lower pricing tiers and volume discounts.7:42–10:40 · Nathan as informed peer 7/10 Competition Analysis, Net Negative Churn, and ARPU Growth Nathan displays solid SaaS domain knowledge by defining net negative churn accurately for the audience and pressing on specific triggers for ARPU expansion.10:40–12:41 · Nathan as informed peer 5/10 Unit Economics, Acquisition Channels, and Team Structure Nathan clarifies Brandon's acronym phrasing (CIC vs CAC) and explores unit economics and marketing channels in an amicable, information-gathering flow.12:41–16:35 · Nathan as informed peer 6/10 Bootstrapping Philosophy and 2016 Revenue Target Nathan explores the capital structure and runs fast mental math on ARR run rate to convert a $15M-$20M target into monthly recurring revenue expectations.16:36–19:33 · Nathan as informed peer 5/10 Company Updates, Contact Information, and HostGator Sponsorship Nathan connects Brandon's sales setup to predictable revenue models, and Brandon corrects Nathan's assumption of monthly rep quota from ARR bookings to MRR equivalence.19:58–23:15 · Nathan as informed peer 5/10 The Famous Five Questions with Brandon Bruce Nathan runs through the Famous Five rapid fire and puts Brandon on the spot with a hypothetical $150M Salesforce buyout question, which Brandon answers thoughtfully.0:59–4:52 · Guest teaching 2/10 Introducing Brandon Bruce and Cirrus Insight High-Level Metrics Nathan directs the flow cleanly, asking Brandon about ARR, team size, and AppExchange ranking tactics while showing he checked the exact review counts beforehand.4:52–7:42 · Guest teaching 4/10 User Metrics, Pricing Tiers, and MRR Figures Nathan attempts quick mental math multiplying 100k seats by $19 ARPU to estimate MRR, but Brandon politely corrects him by pointing out historical lower pricing tiers and volume discounts.7:42–10:40 · Guest teaching 1/10 Competition Analysis, Net Negative Churn, and ARPU Growth Nathan displays solid SaaS domain knowledge by defining net negative churn accurately for the audience and pressing on specific triggers for ARPU expansion.10:40–12:41 · Guest teaching 2/10 Unit Economics, Acquisition Channels, and Team Structure Nathan clarifies Brandon's acronym phrasing (CIC vs CAC) and explores unit economics and marketing channels in an amicable, information-gathering flow.12:41–16:35 · Guest teaching 1/10 Bootstrapping Philosophy and 2016 Revenue Target Nathan explores the capital structure and runs fast mental math on ARR run rate to convert a $15M-$20M target into monthly recurring revenue expectations.16:36–19:33 · Guest teaching 3/10 Company Updates, Contact Information, and HostGator Sponsorship Nathan connects Brandon's sales setup to predictable revenue models, and Brandon corrects Nathan's assumption of monthly rep quota from ARR bookings to MRR equivalence.19:58–23:15 · Guest teaching 1/10 The Famous Five Questions with Brandon Bruce Nathan runs through the Famous Five rapid fire and puts Brandon on the spot with a hypothetical $150M Salesforce buyout question, which Brandon answers thoughtfully.0:59–4:52 · Guest disagreement 0/10 Introducing Brandon Bruce and Cirrus Insight High-Level Metrics Nathan directs the flow cleanly, asking Brandon about ARR, team size, and AppExchange ranking tactics while showing he checked the exact review counts beforehand.4:52–7:42 · Guest disagreement 1/10 User Metrics, Pricing Tiers, and MRR Figures Nathan attempts quick mental math multiplying 100k seats by $19 ARPU to estimate MRR, but Brandon politely corrects him by pointing out historical lower pricing tiers and volume discounts.7:42–10:40 · Guest disagreement 0/10 Competition Analysis, Net Negative Churn, and ARPU Growth Nathan displays solid SaaS domain knowledge by defining net negative churn accurately for the audience and pressing on specific triggers for ARPU expansion.10:40–12:41 · Guest disagreement 0/10 Unit Economics, Acquisition Channels, and Team Structure Nathan clarifies Brandon's acronym phrasing (CIC vs CAC) and explores unit economics and marketing channels in an amicable, information-gathering flow.12:41–16:35 · Guest disagreement 0/10 Bootstrapping Philosophy and 2016 Revenue Target Nathan explores the capital structure and runs fast mental math on ARR run rate to convert a $15M-$20M target into monthly recurring revenue expectations.16:36–19:33 · Guest disagreement 1/10 Company Updates, Contact Information, and HostGator Sponsorship Nathan connects Brandon's sales setup to predictable revenue models, and Brandon corrects Nathan's assumption of monthly rep quota from ARR bookings to MRR equivalence.19:58–23:15 · Guest disagreement 1/10 The Famous Five Questions with Brandon Bruce Nathan runs through the Famous Five rapid fire and puts Brandon on the spot with a hypothetical $150M Salesforce buyout question, which Brandon answers thoughtfully.0:59–4:52 · Nathan pushing back 2/10 Introducing Brandon Bruce and Cirrus Insight High-Level Metrics Nathan directs the flow cleanly, asking Brandon about ARR, team size, and AppExchange ranking tactics while showing he checked the exact review counts beforehand.4:52–7:42 · Nathan pushing back 4/10 User Metrics, Pricing Tiers, and MRR Figures Nathan attempts quick mental math multiplying 100k seats by $19 ARPU to estimate MRR, but Brandon politely corrects him by pointing out historical lower pricing tiers and volume discounts.7:42–10:40 · Nathan pushing back 2/10 Competition Analysis, Net Negative Churn, and ARPU Growth Nathan displays solid SaaS domain knowledge by defining net negative churn accurately for the audience and pressing on specific triggers for ARPU expansion.10:40–12:41 · Nathan pushing back 2/10 Unit Economics, Acquisition Channels, and Team Structure Nathan clarifies Brandon's acronym phrasing (CIC vs CAC) and explores unit economics and marketing channels in an amicable, information-gathering flow.12:41–16:35 · Nathan pushing back 2/10 Bootstrapping Philosophy and 2016 Revenue Target Nathan explores the capital structure and runs fast mental math on ARR run rate to convert a $15M-$20M target into monthly recurring revenue expectations.16:36–19:33 · Nathan pushing back 3/10 Company Updates, Contact Information, and HostGator Sponsorship Nathan connects Brandon's sales setup to predictable revenue models, and Brandon corrects Nathan's assumption of monthly rep quota from ARR bookings to MRR equivalence.19:58–23:15 · Nathan pushing back 3/10 The Famous Five Questions with Brandon Bruce Nathan runs through the Famous Five rapid fire and puts Brandon on the spot with a hypothetical $150M Salesforce buyout question, which Brandon answers thoughtfully.

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

0:00 · Nathan 64.8% · guest 35.2%0:00 · Nathan 64.8% · guest 35.2%3:00 · Nathan 22.3% · guest 77.7%3:00 · Nathan 22.3% · guest 77.7%6:00 · Nathan 26.3% · guest 73.7%6:00 · Nathan 26.3% · guest 73.7%9:00 · Nathan 28.8% · guest 71.2%9:00 · Nathan 28.8% · guest 71.2%12:00 · Nathan 28% · guest 72%12:00 · Nathan 28% · guest 72%15:00 · Nathan 50.4% · guest 49.6%15:00 · Nathan 50.4% · guest 49.6%18:00 · Nathan 55.8% · guest 44.2%18:00 · Nathan 55.8% · guest 44.2%21:00 · Nathan 26.6% · guest 73.4%21:00 · Nathan 26.6% · guest 73.4%24:00 · Nathan 93.1% · guest 6.9%24:00 · Nathan 93.1% · guest 6.9%
Sharpest disagreement ▶ 6:56 Pushing back on simplified revenue multiplication

Brandon politely but firmly shuts down Nathan's attempt to multiply total seats directly by top-tier price to estimate MRR.

 Hardest push from Nathan ▶ 21:47 Probing sleep routine logic

Nathan challenges Brandon's claim of intentionally avoiding eight hours of sleep to understand the founder's daily productivity logic.

 Biggest teaching moment ▶ 7:00 Explaining seat discounting and legacy SaaS pricing

Brandon educates Nathan on why total active seats cannot be directly multiplied by modern tier pricing due to early grandfathered rates and enterprise volume discounts.

 Nathan holds their own ▶ 9:33 Nathan defines net negative churn mechanics

Nathan articulates the technical mechanics of net negative churn and expansion revenue clearly for the audience without needing assistance from the guest.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Brandon Bruce and Cirrus Insight High-Level Metrics 6202 Nathan directs the flow cleanly, asking Brandon about ARR, team size, and AppExchange ranking tactics while showing he checked the exact review counts beforehand.
User Metrics, Pricing Tiers, and MRR Figures 5414 Nathan attempts quick mental math multiplying 100k seats by $19 ARPU to estimate MRR, but Brandon politely corrects him by pointing out historical lower pricing tiers and volume discounts.
Competition Analysis, Net Negative Churn, and ARPU Growth 7102 Nathan displays solid SaaS domain knowledge by defining net negative churn accurately for the audience and pressing on specific triggers for ARPU expansion.
Unit Economics, Acquisition Channels, and Team Structure 5202 Nathan clarifies Brandon's acronym phrasing (CIC vs CAC) and explores unit economics and marketing channels in an amicable, information-gathering flow.
Bootstrapping Philosophy and 2016 Revenue Target 6102 Nathan explores the capital structure and runs fast mental math on ARR run rate to convert a $15M-$20M target into monthly recurring revenue expectations.
Company Updates, Contact Information, and HostGator Sponsorship 5313 Nathan connects Brandon's sales setup to predictable revenue models, and Brandon corrects Nathan's assumption of monthly rep quota from ARR bookings to MRR equivalence.
The Famous Five Questions with Brandon Bruce 5113 Nathan runs through the Famous Five rapid fire and puts Brandon on the spot with a hypothetical $150M Salesforce buyout question, which Brandon answers thoughtfully.

Statements from this episode (14)

Assertion Supported
Latka: Cirrus Insight is Salesforce AppExchange's second-highest rated sales app
“Cirrus insight is the second highest rated sales application of all time on the Salesforce app exchange.”
Nathan Latka Apr 4, 2016 ▶ 1:24
Insight
Bruce: Seat-level reviews help end-user SaaS apps rank higher on AppExchange
“One of the things that helps us the most is that we are an end user based application. So you don't install Serious Insight just once for your org. Instead, if you've got a thousand salespeople, they will all use Serious Insight. And we benefit from that becau…”
Brandon Bruce Apr 4, 2016 ▶ 3:58
Assertion Not checkable as stated
Cirrus Insight serves 100k 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 Apr 4, 2016 ▶ 5:53
Assertion Not checkable as stated
Cirrus Insight exited 2015 at roughly $640k in MRR
“So the, so MRR, we finished 2015 at around six 40 K.”
Brandon Bruce Apr 4, 2016 ▶ 7:31
Assertion Not checkable as stated
Bruce: Cirrus Insight Maintains Net Negative Churn
“So net negative churn. So we always add more seats then we lose, you know, the primary reasons.”
Brandon Bruce Apr 4, 2016 ▶ 8:59
Assertion Not checkable as stated
Cirrus Insight reports LTV of $750-$800 and CAC of $85
“So our LTV right now is between 758 hundred dollars. You know, cost of customer acquisitions about 85 bucks.”
Brandon Bruce Apr 4, 2016 ▶ 10:58
Disclosure
Cirrus Insight finds events and partner marketing outperform ads
“No, we do very little in the way of ads. We do find retargeting to be valuable for us. We certainly tried a lot of different types of advertising, but our most our best spend has been on events and as well as partner marketing.”
Brandon Bruce Apr 4, 2016 ▶ 11:26
Assertion Not checkable as stated
Cirrus Insight maintains a partner network of over 350 consultants
“So we have a network of over 350 consulting partners as well as some resellers.”
Brandon Bruce Apr 4, 2016 ▶ 11:42
Disclosure
Bruce: Cirrus Insight raised $1.15M via convertible notes without institutional VCs
“We've benefited from the, you know, early support of friends and family. And then a few early customers and angels came in to provide some early capital, but otherwise, you know, we consider ourselves bootstrapping institutional backing. Yeah, we just did conv…”
Brandon Bruce Apr 4, 2016 ▶ 13:02
Prediction Didn’t hold up
Bruce: Cirrus Insight targets finishing 2016 at a $15M to $20M run rate
“We've set our sights on doing, you know, about sixteen million in bookings or so. So oftentimes we'll, we'll, we'll look at top line bookings for the sales team. So trying to get those deals in the door, some of them may be multi-year but we love those all the…”
Brandon Bruce Apr 4, 2016 ▶ 15:17
Assertion Supported
Bruce: Outlook represents 75% of the market with customers 4-5x larger than Google
“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 Apr 4, 2016 ▶ 16:02
Disclosure
Bruce: Aaron Ross is an advisor to Cirrus Insight
“And in fact, Aaron Ross is an advisor for us.”
Brandon Bruce Apr 4, 2016 ▶ 18:43
Disclosure
Bruce: Cirrus Insight AEs target $50K monthly bookings quota
“Well, it'd be 50 K in, in booking. So spread, if we were translated into MRR, it'd be a little over four K.”
Brandon Bruce Apr 4, 2016 ▶ 19:24
Disclosure
Bruce: Cirrus Insight acquired Assistant.to about nine months ago
“We acquired them already about nine months ago. We added the functionality into Sears Insight. It's one of our most popular features.”
Brandon Bruce Apr 4, 2016 ▶ 21:23
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