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Jun 1, 2021 · 19m · top-founders

LivingSecurity SaaS Breaks $3m ARR, 150% Retention, New Unify Product To Create More Insights for Security Leaders

Ashley Rose · 10m spoken Nathan Latka · 7m spoken
0:00 / 0:00

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

Living Security CEO Ashley Rose joins Nathan Latka to discuss scaling the cybersecurity human risk platform past $3M in ARR, raising a $14M Series B, launching the enterprise-grade Unify behavioral intelligence platform, and achieving 150% net revenue retention.

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 41.3% of the talking time here. How this is scored →

Nathan as informed peer 6.5 Guest teaching 2.8 Guest disagreement 1.3 Nathan pushing back 2.8
05100:0010:004:18–8:56 · Nathan as informed peer 7/10 Fundraising History, Customer Scale, and Revenue Targets Nathan recalls historical metrics from their 2019 interview, calculates current ARR run rates on the fly from ACV and customer numbers, and asks Ashley to confirm growth trajectories. Ashley is collaborative, confirming the math and growth targets.8:59–13:56 · Nathan as informed peer 6/10 Sponsor Message: Global Remote Team Management with Remote.com Following a sponsor read, Ashley educates Nathan on behavioral human risk metrics beyond simple phishing tests to explain their new Unify product. Nathan probes into the specific user behaviors and enterprise monetization potential.13:56–16:20 · Nathan as informed peer 6/10 Organizational Growth, Ukrainian Dev Shop, and Quota Design Nathan drills into team distribution, clarifying contractor arrangements in Ukraine, and questions the risk of putting CSMs on quotas. Ashley explains her philosophy of aligning CSM quotas with customer empowerment.16:20–19:13 · Nathan as informed peer 7/10 Net Dollar Retention, Capital Deployment, and Payback Dynamics Nathan breaks down net retention mechanics and CAC payback periods based on past disclosures. Ashley agrees with his breakdown and confirms payback expectations will lengthen as they build out category awareness.4:18–8:56 · Guest teaching 2/10 Fundraising History, Customer Scale, and Revenue Targets Nathan recalls historical metrics from their 2019 interview, calculates current ARR run rates on the fly from ACV and customer numbers, and asks Ashley to confirm growth trajectories. Ashley is collaborative, confirming the math and growth targets.8:59–13:56 · Guest teaching 4/10 Sponsor Message: Global Remote Team Management with Remote.com Following a sponsor read, Ashley educates Nathan on behavioral human risk metrics beyond simple phishing tests to explain their new Unify product. Nathan probes into the specific user behaviors and enterprise monetization potential.13:56–16:20 · Guest teaching 3/10 Organizational Growth, Ukrainian Dev Shop, and Quota Design Nathan drills into team distribution, clarifying contractor arrangements in Ukraine, and questions the risk of putting CSMs on quotas. Ashley explains her philosophy of aligning CSM quotas with customer empowerment.16:20–19:13 · Guest teaching 2/10 Net Dollar Retention, Capital Deployment, and Payback Dynamics Nathan breaks down net retention mechanics and CAC payback periods based on past disclosures. Ashley agrees with his breakdown and confirms payback expectations will lengthen as they build out category awareness.4:18–8:56 · Guest disagreement 1/10 Fundraising History, Customer Scale, and Revenue Targets Nathan recalls historical metrics from their 2019 interview, calculates current ARR run rates on the fly from ACV and customer numbers, and asks Ashley to confirm growth trajectories. Ashley is collaborative, confirming the math and growth targets.8:59–13:56 · Guest disagreement 1/10 Sponsor Message: Global Remote Team Management with Remote.com Following a sponsor read, Ashley educates Nathan on behavioral human risk metrics beyond simple phishing tests to explain their new Unify product. Nathan probes into the specific user behaviors and enterprise monetization potential.13:56–16:20 · Guest disagreement 2/10 Organizational Growth, Ukrainian Dev Shop, and Quota Design Nathan drills into team distribution, clarifying contractor arrangements in Ukraine, and questions the risk of putting CSMs on quotas. Ashley explains her philosophy of aligning CSM quotas with customer empowerment.16:20–19:13 · Guest disagreement 1/10 Net Dollar Retention, Capital Deployment, and Payback Dynamics Nathan breaks down net retention mechanics and CAC payback periods based on past disclosures. Ashley agrees with his breakdown and confirms payback expectations will lengthen as they build out category awareness.4:18–8:56 · Nathan pushing back 3/10 Fundraising History, Customer Scale, and Revenue Targets Nathan recalls historical metrics from their 2019 interview, calculates current ARR run rates on the fly from ACV and customer numbers, and asks Ashley to confirm growth trajectories. Ashley is collaborative, confirming the math and growth targets.8:59–13:56 · Nathan pushing back 2/10 Sponsor Message: Global Remote Team Management with Remote.com Following a sponsor read, Ashley educates Nathan on behavioral human risk metrics beyond simple phishing tests to explain their new Unify product. Nathan probes into the specific user behaviors and enterprise monetization potential.13:56–16:20 · Nathan pushing back 4/10 Organizational Growth, Ukrainian Dev Shop, and Quota Design Nathan drills into team distribution, clarifying contractor arrangements in Ukraine, and questions the risk of putting CSMs on quotas. Ashley explains her philosophy of aligning CSM quotas with customer empowerment.16:20–19:13 · Nathan pushing back 2/10 Net Dollar Retention, Capital Deployment, and Payback Dynamics Nathan breaks down net retention mechanics and CAC payback periods based on past disclosures. Ashley agrees with his breakdown and confirms payback expectations will lengthen as they build out category awareness.

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

0:00 · Nathan 72.3% · guest 27.7%0:00 · Nathan 72.3% · guest 27.7%3:00 · Nathan 23.2% · guest 76.8%3:00 · Nathan 23.2% · guest 76.8%6:00 · Nathan 43.1% · guest 56.9%6:00 · Nathan 43.1% · guest 56.9%9:00 · Nathan 57.7% · guest 42.3%9:00 · Nathan 57.7% · guest 42.3%12:00 · Nathan 24.2% · guest 75.8%12:00 · Nathan 24.2% · guest 75.8%15:00 · Nathan 32.4% · guest 67.6%15:00 · Nathan 32.4% · guest 67.6%18:00 · Nathan 26.6% · guest 73.4%18:00 · Nathan 26.6% · guest 73.4%
Sharpest disagreement ▶ 15:30 Defending quota structure for CSMs

Ashley pushes back against Nathan's skepticism that quota-carrying CSMs will overly pressure customers, arguing it builds partnership.

 Hardest push from Nathan ▶ 15:30 Challenging customer success sales quotas

Nathan flags quota-carrying CSMs as a dangerous practice that can incentivize bad sales behaviors.

 Biggest teaching moment ▶ 11:32 Explaining behavioral telemetry beyond phishing

Ashley breaks down how modern security awareness goes beyond phishing tests to track VPN usage, password hygiene, and browsing behaviors.

 Nathan holds their own ▶ 16:39 Deconstructing 150% net retention into churn and expansion

Nathan instantly backs out the math of less than 5% churn and over 50% expansion to explain Ashley's 150% net dollar retention metric.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Fundraising History, Customer Scale, and Revenue Targets 7213 Nathan recalls historical metrics from their 2019 interview, calculates current ARR run rates on the fly from ACV and customer numbers, and asks Ashley to confirm growth trajectories. Ashley is collaborative, confirming the math and growth targets.
Sponsor Message: Global Remote Team Management with Remote.com 6412 Following a sponsor read, Ashley educates Nathan on behavioral human risk metrics beyond simple phishing tests to explain their new Unify product. Nathan probes into the specific user behaviors and enterprise monetization potential.
Organizational Growth, Ukrainian Dev Shop, and Quota Design 6324 Nathan drills into team distribution, clarifying contractor arrangements in Ukraine, and questions the risk of putting CSMs on quotas. Ashley explains her philosophy of aligning CSM quotas with customer empowerment.
Net Dollar Retention, Capital Deployment, and Payback Dynamics 7212 Nathan breaks down net retention mechanics and CAC payback periods based on past disclosures. Ashley agrees with his breakdown and confirms payback expectations will lengthen as they build out category awareness.

Statements from this episode (10)

Assertion Not checkable as stated
Rose: Living Security serves about 130 corporate customers
“We're about 130 different customers”
Ashley Rose Jun 1, 2021 ▶ 4:40
Assertion Supported
Rose: Living Security closed a $14M Series B in March 2021
“We closed our fourteen million dollar series B in March of this year.”
Ashley Rose Jun 1, 2021 ▶ 5:45
Assertion Not checkable as stated
Rose: Living Security's ACV is between $25K and $35K
“ACV is still in the 25 to 35,000 dollar range.”
Ashley Rose Jun 1, 2021 ▶ 7:10
Assertion Not checkable as stated
Rose: Living Security generates over $250K in monthly revenue
“So we're over that.”
Ashley Rose Jun 1, 2021 ▶ 8:22
Prediction Not checkable as stated
Rose: Living Security will exceed $1M monthly revenue in 12 months
“In the next 12 months, yes.”
Ashley Rose Jun 1, 2021 ▶ 8:55
Disclosure
Rose: Living Security aims to upsell Unify to 25-50% of customers
“Over the next 12 months, we're targeting anywhere from, you know, 25 to 50% of our customer base, really selling Unify into, and then expand from there.”
Ashley Rose Jun 1, 2021 ▶ 13:47
Disclosure
Rose: Living Security employs 60 core staff and 15 Ukrainian developers
“We have 60 people on our team, and then we have about 15 engineers and developers in Ukraine.”
Ashley Rose Jun 1, 2021 ▶ 14:04
Disclosure
Rose: Living Security assigns expansion quotas to four Customer Success Managers
“We've got five account executives. We've got six BDRs and then our CSM team also carries a quota from an, from a growth and install based upsell perspective. And we've got four CSMs that carry quotas right now.”
Ashley Rose Jun 1, 2021 ▶ 15:14
Assertion Not checkable as stated
Rose: Living Security reached about 150% net revenue retention last year
“So last year's numbers were about 150% net revenue retention.”
Ashley Rose Jun 1, 2021 ▶ 16:29
Assertion Not checkable as stated
Rose: Living Security lost only one software customer last year
“So our, from a software perspective well, we lost one customer on our software last year.”
Ashley Rose Jun 1, 2021 ▶ 16:40
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