Jan 22, 2025 · 34m · saastr

What to Expect from a New CRO with Kathy Lord, CRO at Zensai

Kathy Lord · 21m spoken Jason Lemkin · 9m spoken
0:00 / 0:00
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In this SaaStr Workshop Wednesday session, Jason Lemkin and Zensai CRO Kathy Lord break down how founders and incoming revenue executives can prevent misalignment, structure realistic first-year onboarding milestones, and align go-to-market strategies across different stages of SaaS growth.

How this conversation actually went

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

Jason as informed peer 3.3 Guest teaching 4.0 Guest disagreement 0.6 Jason pushing back 0.6
05100:0010:0020:0030:000:00–5:04 · Jason as informed peer 6/10 Debating Demand Generation Ownership at the CRO Level Lemkin opens with an introductory question and a detailed personal thesis on executive alignment and 90-day plans before handing off to Lord. The tone is highly collaborative and sets up the workshop agenda.5:04–7:34 · Jason as informed peer 0/10 Understanding Founder Expectations Across Startup Growth Stages Lord delivers a solo presentation monologue detailing CEO expectations across varying ARR stages from product-market fit to scale. Because the host does not speak, host metrics are scored at zero.7:35–12:44 · Jason as informed peer 0/10 Evaluating CRO Milestones in the First 90 Days Lord outlines her specific 90-day checklist for a new CRO, including external customer conversations, pipeline hygiene, and the four operational swim lanes. The segment is an uninterrupted pedagogical monologue.12:46–16:02 · Jason as informed peer 0/10 Contrasting Roles and Establishing Funnel Measurement Models Lord continues her presentation, contrasting tactical VP of Sales duties against strategic CRO responsibilities and introducing multi-quarter transformation roadmaps. The host does not participate in this segment.16:04–22:19 · Jason as informed peer 0/10 Three Pillars for Executive Alignment and Success Lord covers her core framework of clarity, alignment, and empowerment, warning founders against creating decision bottlenecks or protecting sacred cows. The monologue contains no host participation.22:19–25:12 · Jason as informed peer 6/10 Validating Revenue Models and Slowing Offer Closures Lemkin drills into Lord's onboarding experience at Zensai and offers tactical guidance on signing offer letters early while granting candidates time to diligence multi-year models. Lord agrees completely with the methodology.25:13–28:00 · Jason as informed peer 6/10 Analyzing Demand Generation Reporting Under Sales Leadership Lord argues demand gen should generally not sit under a CRO to avoid diluting revenue focus, while Lemkin adds nuance on why modern aggressive sales leaders sometimes demand ownership of top-of-funnel pipeline.28:01–31:33 · Jason as informed peer 6/10 Navigating Leadership Hierarchy and Topping Sales VPs Lord and Lemkin discuss managing incumbent VPs of Sales when hiring a CRO above them. Lemkin cites his classic SaaStr frameworks and examples of decacorn executives who grew after being topped.31:36–34:03 · Jason as informed peer 6/10 Retaining Founder Engagement in Strategic Sales Execution Lemkin asks how to keep product-focused founders engaged in sales after hiring a commercial leader. Lord gives the rule of thumb of committing 10-20% time to key deals, which Lemkin enthusiastically reinforces.0:00–5:04 · Guest teaching 2/10 Debating Demand Generation Ownership at the CRO Level Lemkin opens with an introductory question and a detailed personal thesis on executive alignment and 90-day plans before handing off to Lord. The tone is highly collaborative and sets up the workshop agenda.5:04–7:34 · Guest teaching 5/10 Understanding Founder Expectations Across Startup Growth Stages Lord delivers a solo presentation monologue detailing CEO expectations across varying ARR stages from product-market fit to scale. Because the host does not speak, host metrics are scored at zero.7:35–12:44 · Guest teaching 6/10 Evaluating CRO Milestones in the First 90 Days Lord outlines her specific 90-day checklist for a new CRO, including external customer conversations, pipeline hygiene, and the four operational swim lanes. The segment is an uninterrupted pedagogical monologue.12:46–16:02 · Guest teaching 6/10 Contrasting Roles and Establishing Funnel Measurement Models Lord continues her presentation, contrasting tactical VP of Sales duties against strategic CRO responsibilities and introducing multi-quarter transformation roadmaps. The host does not participate in this segment.16:04–22:19 · Guest teaching 6/10 Three Pillars for Executive Alignment and Success Lord covers her core framework of clarity, alignment, and empowerment, warning founders against creating decision bottlenecks or protecting sacred cows. The monologue contains no host participation.22:19–25:12 · Guest teaching 2/10 Validating Revenue Models and Slowing Offer Closures Lemkin drills into Lord's onboarding experience at Zensai and offers tactical guidance on signing offer letters early while granting candidates time to diligence multi-year models. Lord agrees completely with the methodology.25:13–28:00 · Guest teaching 3/10 Analyzing Demand Generation Reporting Under Sales Leadership Lord argues demand gen should generally not sit under a CRO to avoid diluting revenue focus, while Lemkin adds nuance on why modern aggressive sales leaders sometimes demand ownership of top-of-funnel pipeline.28:01–31:33 · Guest teaching 3/10 Navigating Leadership Hierarchy and Topping Sales VPs Lord and Lemkin discuss managing incumbent VPs of Sales when hiring a CRO above them. Lemkin cites his classic SaaStr frameworks and examples of decacorn executives who grew after being topped.31:36–34:03 · Guest teaching 3/10 Retaining Founder Engagement in Strategic Sales Execution Lemkin asks how to keep product-focused founders engaged in sales after hiring a commercial leader. Lord gives the rule of thumb of committing 10-20% time to key deals, which Lemkin enthusiastically reinforces.0:00–5:04 · Guest disagreement 1/10 Debating Demand Generation Ownership at the CRO Level Lemkin opens with an introductory question and a detailed personal thesis on executive alignment and 90-day plans before handing off to Lord. The tone is highly collaborative and sets up the workshop agenda.5:04–7:34 · Guest disagreement 0/10 Understanding Founder Expectations Across Startup Growth Stages Lord delivers a solo presentation monologue detailing CEO expectations across varying ARR stages from product-market fit to scale. Because the host does not speak, host metrics are scored at zero.7:35–12:44 · Guest disagreement 0/10 Evaluating CRO Milestones in the First 90 Days Lord outlines her specific 90-day checklist for a new CRO, including external customer conversations, pipeline hygiene, and the four operational swim lanes. The segment is an uninterrupted pedagogical monologue.12:46–16:02 · Guest disagreement 0/10 Contrasting Roles and Establishing Funnel Measurement Models Lord continues her presentation, contrasting tactical VP of Sales duties against strategic CRO responsibilities and introducing multi-quarter transformation roadmaps. The host does not participate in this segment.16:04–22:19 · Guest disagreement 0/10 Three Pillars for Executive Alignment and Success Lord covers her core framework of clarity, alignment, and empowerment, warning founders against creating decision bottlenecks or protecting sacred cows. The monologue contains no host participation.22:19–25:12 · Guest disagreement 1/10 Validating Revenue Models and Slowing Offer Closures Lemkin drills into Lord's onboarding experience at Zensai and offers tactical guidance on signing offer letters early while granting candidates time to diligence multi-year models. Lord agrees completely with the methodology.25:13–28:00 · Guest disagreement 2/10 Analyzing Demand Generation Reporting Under Sales Leadership Lord argues demand gen should generally not sit under a CRO to avoid diluting revenue focus, while Lemkin adds nuance on why modern aggressive sales leaders sometimes demand ownership of top-of-funnel pipeline.28:01–31:33 · Guest disagreement 1/10 Navigating Leadership Hierarchy and Topping Sales VPs Lord and Lemkin discuss managing incumbent VPs of Sales when hiring a CRO above them. Lemkin cites his classic SaaStr frameworks and examples of decacorn executives who grew after being topped.31:36–34:03 · Guest disagreement 0/10 Retaining Founder Engagement in Strategic Sales Execution Lemkin asks how to keep product-focused founders engaged in sales after hiring a commercial leader. Lord gives the rule of thumb of committing 10-20% time to key deals, which Lemkin enthusiastically reinforces.0:00–5:04 · Jason pushing back 1/10 Debating Demand Generation Ownership at the CRO Level Lemkin opens with an introductory question and a detailed personal thesis on executive alignment and 90-day plans before handing off to Lord. The tone is highly collaborative and sets up the workshop agenda.5:04–7:34 · Jason pushing back 0/10 Understanding Founder Expectations Across Startup Growth Stages Lord delivers a solo presentation monologue detailing CEO expectations across varying ARR stages from product-market fit to scale. Because the host does not speak, host metrics are scored at zero.7:35–12:44 · Jason pushing back 0/10 Evaluating CRO Milestones in the First 90 Days Lord outlines her specific 90-day checklist for a new CRO, including external customer conversations, pipeline hygiene, and the four operational swim lanes. The segment is an uninterrupted pedagogical monologue.12:46–16:02 · Jason pushing back 0/10 Contrasting Roles and Establishing Funnel Measurement Models Lord continues her presentation, contrasting tactical VP of Sales duties against strategic CRO responsibilities and introducing multi-quarter transformation roadmaps. The host does not participate in this segment.16:04–22:19 · Jason pushing back 0/10 Three Pillars for Executive Alignment and Success Lord covers her core framework of clarity, alignment, and empowerment, warning founders against creating decision bottlenecks or protecting sacred cows. The monologue contains no host participation.22:19–25:12 · Jason pushing back 1/10 Validating Revenue Models and Slowing Offer Closures Lemkin drills into Lord's onboarding experience at Zensai and offers tactical guidance on signing offer letters early while granting candidates time to diligence multi-year models. Lord agrees completely with the methodology.25:13–28:00 · Jason pushing back 2/10 Analyzing Demand Generation Reporting Under Sales Leadership Lord argues demand gen should generally not sit under a CRO to avoid diluting revenue focus, while Lemkin adds nuance on why modern aggressive sales leaders sometimes demand ownership of top-of-funnel pipeline.28:01–31:33 · Jason pushing back 1/10 Navigating Leadership Hierarchy and Topping Sales VPs Lord and Lemkin discuss managing incumbent VPs of Sales when hiring a CRO above them. Lemkin cites his classic SaaStr frameworks and examples of decacorn executives who grew after being topped.31:36–34:03 · Jason pushing back 0/10 Retaining Founder Engagement in Strategic Sales Execution Lemkin asks how to keep product-focused founders engaged in sales after hiring a commercial leader. Lord gives the rule of thumb of committing 10-20% time to key deals, which Lemkin enthusiastically reinforces.

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

0:00 · Jason 68.5% · guest 31.5%0:00 · Jason 68.5% · guest 31.5%3:00 · Jason 68.7% · guest 31.3%3:00 · Jason 68.7% · guest 31.3%6:00 · Jason 0% · guest 100%6:00 · Jason 0% · guest 100%9:00 · Jason 0% · guest 100%9:00 · Jason 0% · guest 100%12:00 · Jason 0% · guest 100%12:00 · Jason 0% · guest 100%15:00 · Jason 0% · guest 100%15:00 · Jason 0% · guest 100%18:00 · Jason 0% · guest 100%18:00 · Jason 0% · guest 100%21:00 · Jason 44.7% · guest 55.3%21:00 · Jason 44.7% · guest 55.3%24:00 · Jason 57.9% · guest 42.1%24:00 · Jason 57.9% · guest 42.1%27:00 · Jason 58% · guest 42%27:00 · Jason 58% · guest 42%30:00 · Jason 48.1% · guest 51.9%30:00 · Jason 48.1% · guest 51.9%33:00 · Jason 64.6% · guest 35.4%33:00 · Jason 64.6% · guest 35.4%
Sharpest disagreement ▶ 25:40 Rejecting demand gen under the CRO

Lord takes a clear, contrarian stance against standard practice by arguing that placing demand generation under sales dilutes focus and alters revenue team culture.

Hardest push from Jason ▶ 26:40 Lemkin pushing modern CRO pipeline ownership

Lemkin nuances Lord's view by pointing out that aggressive modern sales leaders insist on owning demand generation rather than relying on underperforming marketing teams.

Biggest teaching moment ▶ 19:40 Educating founders on sacred cows and autonomy

Lord provides deep operational advice on the necessity of empowering new revenue leaders and eliminating protected internal systems or legacy personnel.

Jason holds their own ▶ 24:05 Lemkin's pre-close diligence playbook

Lemkin demonstrates veteran domain expertise by detailing how boards and founders should slow down final-round candidate evaluation to test indirect revenue risks.

the scores for every segment, with the reasoning behind each
ChapterTopicJason as informed peerGuest teachingGuest disagreementJason pushing backWhy
Debating Demand Generation Ownership at the CRO Level 6211 Lemkin opens with an introductory question and a detailed personal thesis on executive alignment and 90-day plans before handing off to Lord. The tone is highly collaborative and sets up the workshop agenda.
Understanding Founder Expectations Across Startup Growth Stages 0500 Lord delivers a solo presentation monologue detailing CEO expectations across varying ARR stages from product-market fit to scale. Because the host does not speak, host metrics are scored at zero.
Evaluating CRO Milestones in the First 90 Days 0600 Lord outlines her specific 90-day checklist for a new CRO, including external customer conversations, pipeline hygiene, and the four operational swim lanes. The segment is an uninterrupted pedagogical monologue.
Contrasting Roles and Establishing Funnel Measurement Models 0600 Lord continues her presentation, contrasting tactical VP of Sales duties against strategic CRO responsibilities and introducing multi-quarter transformation roadmaps. The host does not participate in this segment.
Three Pillars for Executive Alignment and Success 0600 Lord covers her core framework of clarity, alignment, and empowerment, warning founders against creating decision bottlenecks or protecting sacred cows. The monologue contains no host participation.
Validating Revenue Models and Slowing Offer Closures 6211 Lemkin drills into Lord's onboarding experience at Zensai and offers tactical guidance on signing offer letters early while granting candidates time to diligence multi-year models. Lord agrees completely with the methodology.
Analyzing Demand Generation Reporting Under Sales Leadership 6322 Lord argues demand gen should generally not sit under a CRO to avoid diluting revenue focus, while Lemkin adds nuance on why modern aggressive sales leaders sometimes demand ownership of top-of-funnel pipeline.
Navigating Leadership Hierarchy and Topping Sales VPs 6311 Lord and Lemkin discuss managing incumbent VPs of Sales when hiring a CRO above them. Lemkin cites his classic SaaStr frameworks and examples of decacorn executives who grew after being topped.
Retaining Founder Engagement in Strategic Sales Execution 6300 Lemkin asks how to keep product-focused founders engaged in sales after hiring a commercial leader. Lord gives the rule of thumb of committing 10-20% time to key deals, which Lemkin enthusiastically reinforces.

Statements from this episode (16)

Insight
Lord: CROs should not own demand gen as it dilutes focus
“But I think you dilute the focus of the CRO by having them own that demand gen piece. So the short answer, I don't think it should be part of it because I think it's a different discipline and it changes the culture and focus of the revenue organization.”
Kathy Lord Jan 22, 2025 ▶ 0:41
Insight
Lemkin: Executives flame out from CEO goal misalignment, not lack of ability
“And I see so many executives flame out weeks two through 20 or 50, and it's not that they weren't great. It's just, they were never aligned with the CEO.”
Jason Lemkin Jan 22, 2025 ▶ 3:56
Insight
Lemkin: A veteran executive's playbook never works 100% at a new startup
“And a veteran is naturally gonna wanna bring that playbook into the new company and never does that playbook work a hundred percent. It never works a hundred percent.”
Jason Lemkin Jan 22, 2025 ▶ 4:31
Insight
Lord: Direct customer conversations educate incoming sales leaders more than call recordings
“It doesn't matter how many, you know, recorded videos of customer calls you give them, or how many transcripts, or how many times they talk to the sales or channel teams. Having the direct conversations with those customers or prospects is, is where the majori…”
Kathy Lord Jan 22, 2025 ▶ 9:43
Insight
Lord: VP of Sales executes current pipeline, CRO builds architecture to scale
“Where the VP of sales role is a little bit different is they need to be able to take and work within Where the organization is at today... They are actively in the trenches and engaged in a majority of the key deals. They should be taking a look at the assessm…”
Kathy Lord Jan 22, 2025 ▶ 12:59
Insight
Lord: Incoming revenue leaders must build a multi-quarter plan in 90 days
“You need to have more than the 90 day plan developed in that first 90 days, right? So this is where it's really critical and it really helps you make sure that you're focused on the things that are going to move the needles and that everybody has clarity in th…”
Kathy Lord Jan 22, 2025 ▶ 15:36
Insight
Lord: Hiring revenue leaders requires pattern recognition for next growth stage
“And one of the things I've found is the highest indicator of success in bringing somebody in is do they have the pattern recognition for your next stage of growth?”
Kathy Lord Jan 22, 2025 ▶ 17:29
Insight
Lord: Growth stalls when companies protect sacred people, processes, or systems
“There can't be sacred people, processes, or systems. Or else it's really difficult to drive the level of transformation that you want to scale your business.”
Kathy Lord Jan 22, 2025 ▶ 20:26
Insight
Lemkin: Give CRO candidates signed offers with time to validate plans
“Give them an unsigned off, give them a signed offer letter, but don't ask them to countersign until they're all in that way. The pressure's off, right? Here's your comp. Here's your title. Here's your equity. It's signed. If you need two weeks to make sure you…”
Jason Lemkin Jan 22, 2025 ▶ 24:45
Opinion
Lemkin: Few sales leaders are quant enough to understand demand gen
“I don't know very many sales leaders that intuitively are detail or quant enough to understand demand gen marketing.”
Jason Lemkin Jan 22, 2025 ▶ 26:40
Opinion
Lemkin: Having CS report to a CRO is 'terrible'
“I also didn't want customer success to report to CRO, but I lost that battle, right? That, that ship has sailed. I think it's terrible”
Jason Lemkin Jan 22, 2025 ▶ 26:50
Insight
Lemkin: Demand gen reporting to aggressive sales leaders can sometimes work
“I think it's more whether demand gen should report to an aggressive sales leader who says I've had an all of enough and I used to be against it for the reasons, but now I'm seeing it work up to a point because at least they can get more results versus a lackad…”
Jason Lemkin Jan 22, 2025 ▶ 27:42
Insight
Lord: VPs of Sales should only get soft vetoes on CRO hires
“And I think if you totally trust them and you have a good relationship with them, I think they are a soft veto because the challenge is. They can look for cultural and ability to maybe understand the product or market, but that's likely where their experience …”
Kathy Lord Jan 22, 2025 ▶ 29:52
Insight
Lemkin: Never hire a CRO that everyone on the team loves
“Never, never hire a CRO that everybody loves because there's so much bias across the team. There has to be some, like someone has to be threatened by the CRO or you're not making the right hire.”
Jason Lemkin Jan 22, 2025 ▶ 30:18
Insight
Lord: CEOs must spend 10% to 20% of time with customers
“You should always, regardless of size, the CEO should be actively involved, you know, at least 10% of their time to 20% engaged with customers and partners.”
Kathy Lord Jan 22, 2025 ▶ 32:59
Insight
Lemkin: Hiring a great sales leader gives founders zero time back
“When you hire a great sales leader, assign it, you don't get any time back in sales. It's just used differently. You'll just be more efficient.”
Jason Lemkin Jan 22, 2025 ▶ 33:14
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