Jim Kaskade

As CEO of Conversica for over five years, I approached leadership with a belief that culture drives strategy, and strategy drives execution. That philosophy translated into a hands-on, deeply transparent management style—one that blurred traditional lines between executives, board members, and functional leaders. Across every area of the business, we learned powerful lessons—what worked, what didn’t, and what we would never repeat. These “Dos and Don’ts” aren’t theoretical; they’re forged from the day-to-day reality of building a high-ambition, high-integrity AI company navigating shifting markets, investor expectations, and internal transformation. From engineering to HR, board governance to sales, this simple framework (culture -> strategy -> execution) captures the operating DNA I instilled—and the clarity I demanded—at every level of Conversica.

Executive Team “Dos”

1. Do Lead with Full Ownership
   • Execs were expected to come to weekly meetings and QBRs with command over their area, including performance metrics, problem statements, and proposed solutions.
   • With over 400 design thinking workshops across 23 QBRs, we always came away with clear MBOs/OKRs for the quarter that were aligned across all.
2. Do Embrace Radical Candor
   • Team1 was expected to share both wins and losses transparently, but most importantly, “real issues”. Hiding problems or sugarcoating underperformance was not tolerated.
3. Do Contribute Cross-Functionally
   • Leaders were expected to look beyond their silos—engaging in discussions even if outside their core function.
4. Do Prepare for Every QBR Like a Board Meeting
   • The bar for readiness was high—leaders were expected to bring their largest challenges, drive alignment to OKRs, participate in a quarterly 360 actively, and take away their action items with data-backed plans.
5. Do Challenge and Support Peers
   • Healthy conflict and idea debate were encouraged. Leaders were measured not just on functional success, but also on how they helped elevate peers.
6. Do Follow Through
   • Assignments, takeaways, and action items from QBRs or executive meetings were tracked and expected to be resolved by the next session.
7. Do Seek Leadership For the Stage
   • Don’t be shy on leadership change based on the company’s needs / stage of the business.
     • Founder operating role removed
     • Three heads of legal (Johnson -> Fadli -> Barr)
     • Four CS leaders (Kaminski -> Hansen -> Dillon -> Oilman)
     • Three CTO/VP Engineering leaders (Koepf -> Jancola -> Jegan)
     • Five CPO/VP Product leaders (Webb-Purkis -> Reddy -> Azimi -> Laraki -> Etchieson)
     • Two CMOs (Vittal -> Greenberg)
     • Five VP Direct Sales (Marod -> McLaughlin -> Banuelos -> Sunando -> Pasco)
     • Four VP Indirect Sales (McCraith -> Fox -> Sunando -> Pasco)
     • Four CFOs (Lund -> Maloney -> Driscoll -> Lockinger)

Executive Team “Don’ts”

1. Don’t Operate in a Silo
   • Functional leaders were called out for being too insular or detached from company-wide priorities or cross-functional planning.
2. Don’t Wait for Permission
   • Leaders were discouraged from being passive. Waiting for CEO instructions instead of taking initiative was seen as a red flag.
3. Don’t Undermine Unity
   • Going offline or back-channeling decisions that were made in QBRs or weekly syncs was not tolerated. Unified messaging post-meetings was a norm.
4. Don’t Under-Prepare
   • Surfacing challenges without ideas on a proposed path forward or data backing was flagged as poor executive behavior.
5. Don’t Tolerate Mediocrity
   • Team1 culture demanded high standards. Tolerating underperformance in one’s team or in peer teams was seen as a leadership failure.
6. Don’t Avoid Hard Conversations
   • Whether it was a misaligned strategy, team conflict, or failed execution, execs were expected to engage constructively and directly—not sidestep issues.
     

These cultural and behavioral expectations created a high-functioning executive team that mirrored the transparency and intensity modeled from the top.

Direct Sales “Dos”

1. Do Prioritize Profitability Over Volume
   • Structure deals with clear ROI and unit economics; focus on long-term margin and LTV, not just win rates.
2. Do Align Sales Structure with Target Market
   • Enterprise sales require enterprise reps. Field reps brought credibility and strategic engagement to complex deals.
3. Do Specialize by Vertical (Industry) and Segment (ENT, Mid-Market, vs SMB)
   • Leveraging vertical expertise (especially beyond Automotive) improved deal quality and rep effectiveness.
4. Do Integrate Tightly with Marketing and CS
   • Coordinated handoffs and consistent messaging ensured smoother onboarding and higher retention.
5. Do Set Realistic, Tiered Quotas
   • 80% achievement in 4Q24 and 90% in 1Q25 demonstrated that calibrated targets motivated performance without setting teams up to fail.
6. Do Track Sales Efficiency Metrics
   • Regularly monitor individual rep achievement, as well as CAC, ACV, sales cycle, ROI and payback period for every deal to ensure ongoing sales health.
     

Direct Sales “Don’ts”

1. Don’t Rely Solely on “dialing for dollars” for Complex Segment Size and/or Verticals
   • Acting like an Inside rep (with zero face-time), closing unprofitable deals, lacked the depth and context needed for sustainable growth.
2. Don’t Sacrifice Deal Quality for Volume
   • Signing deals that don’t make money or retain well is a long-term liability. High-value use cases only! ICP!!!
3. Don’t Operate in Isolation
   • Sales success is not independent; without alignment to Product, Marketing, and CS, selling becomes shortsighted.
4. Don’t Overpromise Product Capabilities
   • Mismatched customer expectations led to implementation friction and early churn.
5. Don’t Set Misaligned Incentives
   • Comp plans that reward bookings without retention thresholds can drive harmful selling behaviors.
6. Don’t Ignore Field Feedback
   • Field reps are closest to customer pain points—ignoring their insights risks product-market misalignment.
     

Sales isn’t just about closing deals—it’s about closing the right deals. At Conversica, we learned that velocity without viability is a fast path to churn. The shift from transactional selling to value-driven partnerships required more than a new comp plan—it demanded a new mindset. In the end, the most successful sales leaders weren’t just hunters; they were architects of long-term customer success.

Indirect Sales “Dos”

1. Do Invest in OEM Partnerships
   • The OEM model (versus Referral, versus Reseller) was the only consistently successful channel, offering predictable pipeline contribution and scalable revenue opportunities.
2. Do Treat Partnerships as Strategic Extensions
   • OEM partners were treated like part of the Conversica go-to-market engine, receiving training, enablement, co-marketing, and product support.
3. Do Focus on Fewer, Deeper Relationships
   • Prioritizing quality over quantity yielded stronger alignment, better integration, and long-term success with a limited number of Partners.
4. Do Build Repeatable GTM Motions
   • Successful partner engagements with defined sales playbooks, onboarding kits, and performance scorecards—mirroring internal GTM rigor.
5. Do Align Incentives and Success Metrics
   • Partners who had mutual revenue targets, customer success goals, and product feedback loops were more engaged and accountable.
6. Do Leverage Referral Learnings for Partner Setup
   • Partner successes help identify key value props and ideal partner profiles that were later codified in OEM onboarding.
     

Indirect Sales “Don’ts”

1. Don’t Over-Invest in Long-Tail Consultancies
   • These firms lacked the scale, focus, and customer overlap necessary to deliver meaningful revenue; enablement costs rarely paid off.
2. Don’t Assume Mid-Market or Regional SIs Will Scale
   • Despite initial interest, these partners often under-delivered due to competing priorities and limited vertical expertise.
3. Don’t Chase Global SI Relationships Without Deep Sponsorship
   • Without strong executive alignment and joint solution packaging, GSIs provided visibility but failed to convert into revenue.
4. Don’t Generalize Partner Enablement
   • Broad training and templated materials weren’t sufficient—partners needed tailored messaging, use cases, and co-sell scripts.
5. Don’t Treat All Partners Equally
   • Time and resources were better spent doubling down on the top-performing Partners than trying to revive underperforming partnerships.
6. Don’t Ignore Product Fit in Partner Strategy
   • Partner success stemmed from tight product integration and use-case alignment; partnerships without this foundation floundered.

Indirect sales isn’t about building a large partner ecosystem—it’s about cultivating the right ecosystem. At Conversica, we discovered that channels don’t scale your business unless they first believe in your value and can deliver it with precision. Our most successful model, OEM, worked because it was a true extension of our strategy—not just a reseller badge. Channel success isn’t measured by logos signed, but by partners who fight alongside you, not just for you.

Marketing “Dos”

1. Do Treat Messaging as a Strategic Weapon
   • We know that effective messaging can determine market winners—this mindset helped shape differentiated positioning that earned Conversica a lead spot in the Forrester Wave.
2. Do Continuously Evolve the Narrative
   • Messaging was regularly iterated to keep pace with market trends and Conversica’s product evolution, from Intelligent Virtual Assistant to Revenue Digital Assistant to Revenue Digital Agents.
3. Do Build Category Leadership
   • Our push to define a new category around “AI-powered workforce” and “RDA (Revenue Digital Agent)” helped Conversica rise above feature comparisons. We scaled revenue, not just focused on reducing costs.
4. Do Embrace Challenger Messaging
   • Marketing was tasked with battling the “status quo” of human-dominated workflows. The narrative had to provoke change, showing AI as not just viable, but superior.
5. Do Align Closely with Product and Sales
   • Strategic marketing wasn’t siloed. Positioning, campaigns, and content were built in tandem with product roadmap and GTM strategy.
6. Do Use Analyst Relations as Leverage
   • We invested in analyst visibility—especially Forrester—to establish Conversica’s credibility and thought leadership, which paid off with category leadership recognition.
     

Marketing “Don’ts”

1. Don’t Assume Feature Parity is Enough
   • Competing on functionality alone, especially against manual/human incumbents, failed to drive behavior change. The battle was emotional, not technical.
2. Don’t Undervalue Change Management Messaging
   • Messaging focused solely on benefits missed the deeper resistance to replacing humans with AI. Without addressing change barriers, adoption stalled.
3. Don’t Underinvest in Brand
   • When brand investment lagged, it diluted Conversica’s leadership potential—despite strong product-market alignment and analyst validation.
4. Don’t Rely on Mainstream AI Content
   • At times, over-indexing on more good content to expand reach and awareness. Bold, controversial messaging was needed to fight “do nothing” inertia.
5. Don’t Ignore Sales Feedback
   • Marketing that misses sales field insights—especially from the Direct Sales evolution—struggles to support later-stage conversion and objection handling.
6. Don’t Treat the Human vs. AI Battle as a Rational Argument
   • Winning over the market required appealing to emotional drivers, not just logical benefits of AI over human labor. We feared the few that would not align with this reality, but maybe “who cares, it’s reality”?

Marketing was our voice, our positioning, and often our first impression. At Conversica, we learned that great messaging doesn’t just attract attention—it shapes belief. Competing with the status quo meant more than generating leads; it meant educating, challenging, and inspiring a market to change behavior. The companies that win aren’t always the ones with the best tech—they’re the ones with the clearest story.

Customer Success “Dos”

1. Do Make Customer Success a Company-Wide Responsibility
   • We institutionalized CS across departments—from Sales to Product—creating shared accountability for retention and satisfaction.
2. Do Continuously Iterate the CSM Model
   • Leadership cycles (4 different heads of CS) reflected ongoing adaptation. Each leader brought new structure, but systemic churn challenges required persistent re-evaluation.
3. Do Elevate Churn Metrics as Primary KPIs
   • Churn and retention were not afterthoughts—they were board-level and QBR-level discussions, signaling their strategic importance.
4. Do Deepen Engagement with Customers Early
   • Programs focused on early onboarding success, value realization within the first 90 days, and proactive health scoring were critical steps forward.
5. Do Invest in Product-Driven Success Tools
   • Success programs started incorporating digital touchpoints, user training modules, and AI insights to scale CSM efforts more efficiently.
     

Customer Success “Don’ts”

1. Don’t Treat Churn as a Departmental Problem
   • Earlier organizational phases leaned too heavily on CSMs alone to fix churn, when issues often stemmed from product gaps or misaligned sales promises.
2. Don’t Ignore Segmentation
   • Failing to tailor CS efforts by segment (Enterprise vs. SMB, Direct vs. Indirect, Auto vs. Tech) led to diluted outcomes and overextension of resources.
3. Don’t Overlook Product Fit as a Churn Driver
   • CS teams were sometimes forced to “save” customers who shouldn’t have been signed in the first place, especially during the early Automotive push.
4. Don’t Assume One Leader Will Fix It All
   • Rotating through four CS leaders underscored that the churn problem was systemic—not just tactical or personnel-driven.
5. Don’t Underestimate Macro Headwinds
   • 2023 was a brutal year for SaaS; Conversica faced compounded pressure due to entering the year with weak retention and leaving it still stabilizing.
6. Don’t Focus Solely on Renewal
   • CSMs had to evolve from reactive renewal managers to strategic account advisors. Lagging here often correlates with surprise churns.

Customer Success was our biggest battlefield—and our greatest teacher. At Conversica, we faced the hard truth that retention isn’t a department’s job; it’s the company’s job. Despite strong intentions and capable leaders, high churn revealed the limits of good service without deep adoption. Real success meant moving from reactive support to proactive transformation—guiding customers not just to use AI, but to trust it enough to change how they work.

Technical Support “Dos”

1. Do Operate as One Leg of the Three-Legged Customer Support Stool
   • TS functioned as a core component alongside Customer Success Managers (CSMs) and Professional Services/TAMs, jointly responsible for customer health and resolution velocity.
2. Do Define Escalation Protocols Clearly
   • Despite overlapping roles, clarity around when and how TS should take over from SEs, CSMs, or TAMs helped manage customer expectations and internal efficiency.
3. Do Foster Tight Collaboration with Engineering
   • TS maintained a high-value role as a conduit between customer issues and Engineering/Product insights—especially for systemic bugs or enhancement requests.
4. Do Provide Structured Handoff Between Pre-Sales and Post-Sales
   • Hand-offs from Solutions Engineers (SEs) to TS were essential in keeping historical context on deployments and custom configurations.
5. Do Track and Prioritize Issue Types
   • TS tickets were increasingly analyzed for trends, helping the business identify root causes across product and process gaps.
     

Technical Support “Don’ts”

1. Don’t Treat TS as a Reactive-Only Function
   • TS became most valuable when empowered to flag patterns proactively—reducing churn and informing roadmap prioritization.
2. Don’t Allow Blurred Role Lines to Delay Resolution
   • In cases where SEs, CSMs, or TAMs overlapped with TS, lack of role clarity could lead to finger-pointing or dropped tickets.
3. Don’t Under-resource the Team
   • TS often operated under the radar but carried a heavy load; staffing and tooling needed periodic reevaluation to keep pace with customer volume and complexity.
4. Don’t Disconnect TS from Strategic Initiatives
   • TS insights were sometimes siloed from broader strategic efforts (e.g., churn reduction, product-market fit improvements), missing chances to shape higher-level strategy.
5. Don’t Neglect Customer Communication Training
   • TS needed not just tech skills but also communication finesse. Poor messaging during support escalations could amplify frustration.
     

Technical Support wasn’t just a ticketing function—it was a key pillar in a complex customer journey. At Conversica, we learned that when support is siloed, the customer feels it first. By integrating TS with CSMs and TAMs, and aligning closely with Product and Engineering, we ensured that customer issues didn’t just get resolved—they informed roadmap and reinforced trust. In an AI-driven solution, precision and empathy in support aren’t optional—they’re foundational.

Professional Services “Dos”

1. Do Align PS Strategy with Channel Model
   • The original plan to lean on partners as an extended PS force was aligned with a lean internal investment model. This made sense from a margin and scale perspective if partner activation succeeded.
2. Do Emphasize the Need for Domain Expertise
   • You correctly identified that PS success in Conversica’s space demanded deep buyer domain knowledge—something generic SaaS PS teams often lack.
3. Do Integrate PS Insights into Product and Success
   • When PS teams were involved, their direct exposure to customer workflows made them valuable feedback loops for improving implementation paths and onboarding design.
4. Do Define PS Scope Explicitly
   • There was effort to clarify the role of PS versus CSM, TS, and SEs, helping to manage internal and customer expectations—even when resources were constrained.
     

Professional Services “Don’ts”

1. Don’t Rely Solely on Channel Partners for PS Execution
   • When the partner network underperformed, the lack of a back-up in-house team meant Conversica was exposed—no one left to do the “change work” of displacing humans with AI.
2. Don’t Underinvest Without Mitigation Plans
   • Industries required consultative selling and deployment. Without internal consultants or partner equivalents, many customers couldn’t visualize the transition from status quo in their own language.
3. Don’t Overestimate Partner Enablement Speed
   • Partners often required more time, incentive, and investment to effectively deliver PS-level support than anticipated.
4. Don’t Ignore Strategic PS as a Differentiator
   • PS could have been a key lever in helping customers imagine new AI workflows and challenge traditional staffing models. This consultative value went uncapitalized.
5. Don’t Separate PS Strategy from Customer Retention
   • Without adequate onboarding and consultative depth, customers struggled with adoption—exacerbating churn and undercutting CS efforts.
     

Professional Services was missed potential leverage. At Conversica, we bet that partners would fill the consulting gap—but when that bet didn’t pay off, we were left without the muscle to challenge customer inertia. In a business where AI replaces human workflows, implementation isn’t just technical—it’s transformational. And transformation demands domain expertise, trust, and a guide. Skimping on PS didn’t just affect delivery—it delayed adoption and diluted outcomes.

Product Management (PM) “Dos”

1. Do Position Product as a Change Agent
   • Recognize that Product-Market-Fit (PMF) in Conversica’s space isn’t about utility alone—it’s about enabling organizational transformation via AI. Product should drive this vision.
2. Do Architect for Configurability
   • Since customers vary widely (“snowflakes”), the product must accommodate flexibility. This requires modular design and strong integration capabilities (unless you’re going narrow with a signal industry, smaller segment size).
3. Do Align Features with Value Realization
   • Every roadmap decision should be evaluated through the lens of, “Does this help the customer experience more ROI faster?”—a theme echoed across time.
4. Do Partner with Sales, CS, and Marketing
   • PM is central to unifying market-facing functions around value propositions, objection handling, and change management.
5. Do Lead with Strategic Vertical Insights
   • As seen in the OEM partner successes, PM should anchor product strategy in vertical-specific pain points, not general functionality.
6. Do Treat PLG as One Input, Not the Strategy
   • PLG can generate signals, but the real path to PMF in Conversica’s space was consultative—not transactional. Product must support this.

Product Management (PM) “Don’ts”

1. Don’t Assume One Size Fits All
   • Early missteps stemmed from assuming a core product could serve SMB and Enterprise with minor adjustments. It couldn’t.
2. Don’t Isolate PM from the Customer Journey
   • Without immersion in post-sale adoption challenges (support, PS, CS), PM risked designing for buyer personas, not users.
3. Don’t Undervalue Change Management Support
   • Even the most powerful feature will fail without tools for enabling process change. PM ignored this at their peril.
4. Don’t Chase Competitors’ Checklists
   • PMF was never about parity—it was about creating new behavior in orgs. Feature-chasing eroded focus and clarity.
5. Don’t Rely Solely on Feedback from Losses
   • PM needed to balance win-path validation with postmortems. Over-rotation on lost deals led to reactive roadmaps.
6. Don’t Ignore the Friction Created by AI Expectations
   • Buyers often expected magic from AI. PM needed to set and manage expectations through transparency and education—an area that faltered when left to sales alone.
     

Product Management at Conversica had the toughest job—bridging the gap between a radically disruptive AI technology and a conservative market anchored in human labor. 

In the beginning when it failed, it was because PM was treated as a feature factory rather than customer transformation leaders.

In the end, when it worked, it was because PM acted not just as builders, but as catalysts for organizational change.

R&D “Dos”

1. Do Burn Down Technical Debt Early
   • Your immediate shift from feature-only velocity to debt prioritization laid the foundation for future scalability, reliability, and innovation.
2. Do Redefine Velocity as a Strategic Metric
   • Velocity wasn’t about shipping volume—it was about delivering value with stability, and that meant investing in the plumbing first.
3. Do Send Engineers into the Field
   • Direct exposure to customer environments helped engineers internalize user pain, which directly led to innovative, leapfrogging solutions.
4. Do Align Engineering with Customer Impact
   • R&D priorities eventually mirrored real-world outcomes—tying roadmap to usage, NPS, and churn reduction rather than just functional completeness.
5. Do Build for Disruption, Not Just Iteration
   • Once stabilized, engineering delivered major platform shifts (e.g., NG Chat) with agility that surprised both customers and competitors.
6. Do Cultivate Cross-Functional Collaboration
   • Engineers worked alongside CS, Sales, and Product—not in silos—leading to faster cycles between problem discovery and resolution.
     

R&D “Don’ts”

1. Don’t Accumulate Hidden Tech Debt
   • Prior to your leadership, debt was accumulated without clear prioritization—stalling velocity and causing reliability issues.
2. Don’t Prioritize Features Over Foundation
   • The early focus on rapid feature delivery without regard to architecture created scaling constraints that had to be retroactively fixed.
3. Don’t Isolate Engineering from Users
   • When engineers were insulated from customer pain, solutions often missed the mark. Direct exposure became a competitive advantage.
4. Don’t Ignore the Strategic Role of Architecture
   • Investments in platform flexibility enabled faster responses to new market demands. Skipping this would have bottlenecked growth.
5. Don’t Allow Backlogs to Obscure Value
   • Engineering backlogs were later cleaned up and realigned to customer value and impact (properly scoring, e.g. RICE)—not just internal wish lists.
6. Don’t Treat Velocity as a Blind Sprint
   • “Velocity” evolved from a brute-force metric to a strategic indicator of engineering readiness, product-market adaptability, and market responsiveness.
     

R&D transformed from a reactive support function into a strategic catalyst for innovation, capable of anticipating customer needs and outpacing competition—anchored by a disciplined attack on technical debt and a cultural shift toward customer intimacy.

Cloud Ops / DevSecOps “Dos”

1. Do Hire Experts and Trust Them
   • I brought in a high-performing leader from a prior company who immediately implemented best-in-class practices without needing oversight.
2. Do Build a “Silent Running” Team
   • Cloud Operations functioned smoothly and quietly—an indication of proactive monitoring, strong infrastructure hygiene, and mature processes.
3. Do Automate Everything
   • The team’s seamless delivery was a result of heavy automation in CI/CD, monitoring, scaling, and remediation.
4. Do Embed Security into DevOps
   • The term “DevSecOps” means that security was not an afterthought—it was baked into development and deployment pipelines from the start.
5. Do Standardize Processes
   • The team’s ability to “do this with their eyes closed” came from consistent, repeatable systems and SOPs that eliminated variability.
6. Do Enable Innovation Through Stability
   • With infrastructure just working, engineering and product teams could focus on building disruptive features without firefighting.
     

Cloud Ops & DevSecOps “Don’ts”

1. Don’t Micromanage a High-Caliber Team
   • We resisted the temptation to over-involve ourselves in a function that was clearly operating at a high level of autonomy and effectiveness.
2. Don’t Overlook Their Strategic Role
   • While low visibility is a success marker, their contribution to uptime, reliability, and customer trust was foundational to the brand.
3. Don’t Treat Security as a Checklist
   • The team implemented security as a core principle, not a box to tick—critical in a world where AI and customer data integrity are paramount.
4. Don’t Leave Incident Management to Chance
   • DevSecOps’ quiet performance came from robust incident response protocols, well-tested DR plans, and proactive threat detection.
5. Don’t Skimp on Observability
   • Even without visible documentation, such performance is only possible with full-stack observability, alerting, and telemetry.
6. Don’t Let Dev and Ops Drift Apart
   • The integration of DevSecOps ensured that developers and operators worked as a unified force, not separate functions.

Cloud Operations or DevSecOps was the quiet strength behind our scalability and trust. At Conversica, we made one of our best decisions early—hiring a proven leader who built a team that ran with confidence and consistency. In a world of always-on AI, customers don’t ask if you’re secure or stable—they assume you are. When you get it right, no one notices. When you don’t, everyone does. We chose to get it right from the start.

Legal & Security “Dos”

1. Do Scale Legal with Process, Not Headcount
   • With only one General Counsel, legal support was scaled through templates, repeatable workflows, and internal enablement—making legal a force multiplier across departments.
2. Do Turn Legal into a Strategic Asset
   • Legal was embedded into sales enablement, marketing messaging, and customer onboarding, enhancing trust and removing friction from deal cycles.
3. Do Champion Security and Compliance as a Company-Wide Priority
   • Even with a single Infosec Director, Conversica cultivated a culture where security wasn’t IT’s job—it was everyone’s responsibility.
4. Do Integrate Legal Early in Go-to-Market
   • Legal was involved at the start of GTM efforts to ensure compliance, reduce downstream risk, and create selling confidence around data and privacy.
5. Do Leverage Compliance for Differentiation
   • Certifications, policies, and audit readiness were used to build customer confidence—particularly in verticals like financial services and education.
6. Do Foster Trust through Transparency
   • Legal and Security helped shape external-facing content (e.g., terms, privacy policies, SOC 2 summaries) into customer-facing trust signals.

Legal & Security “Don’ts”

1. Don’t Let Legal become the Bottleneck
   • Legal was designed not to slow things down but to accelerate execution by pre-clearing pathways and reducing risk through standardization. BTW, privately-held companies can take more risk.
2. Don’t Separate Compliance from Commercial Strategy
   • Our leadership integrated compliance into sales and renewal motions, turning it from overhead into a retention and acquisition lever.
3. Don’t Let Security Become Reactive
   • With clear protocols and company-wide engagement, security stayed proactive and preventive, not just responsive to incidents.
4. Don’t Rely on Ad Hoc Processes
   • The GC’s success stemmed from scalable, repeatable systems—not one-off reviews or high-touch interventions.
5. Don’t Leave Data Handling to Chance
   • InfoSec and Legal worked together to build robust data governance that aligned with evolving customer expectations and global regulations.
6. Don’t Underestimate the Power of Legal in Marketing
   • Legal helped build marketing narratives around trust, safety, and compliance, which were critical differentiators in the AI space.
     

This model showed how even a lean Legal and Security team could punch far above its weight when empowered with automation, process, and cultural alignment.

HR / People “Dos”

1. Do Prioritize Culture Above All Else (it’s #1)
   • You established culture as the company’s operating system—more important than strategy or execution—and reinforced it through people, process, and leadership expectations.
2. Do Treat HR as a Strategic Function
   • HR influenced not just retention or morale, but directly supported GTM performance, organizational alignment, and operational rhythm.
3. Do Embed Core Values into Daily Rituals
   • Culture was operationalized through rituals like monthly all-hands meetings, where company performance, values, and recognition were front and center.
   • Monthly anonymous surveys gathered honest sentiment and held leadership accountable to the employee experience in real time.
4. Do Hire and Promote Based on Culture Fit
   • Leaders and ICs were selected based on values alignment as much as functional expertise—ensuring a consistent behavioral DNA.
5. Do Build Psychological Safety
   • People were encouraged to speak up, challenge ideas, and share failures—creating a high-trust, low-politics environment.
6. Do Recognize and Reward the Right Behaviors
   • Value-aligned behaviors were regularly spotlighted in company meetings, 1:1s, and performance reviews—making culture tangible.
     

HR / People “Don’ts”

1. Don’t Tolerate Toxic or Misaligned Leaders (Fire Fast)
   • Culture violations, regardless of performance, were non-negotiable. Leaders who didn’t embody the values were exited—even if they hit their numbers.
2. Don’t Treat HR as Reactive or Back-Office
   • HR was proactively engaged in strategic planning, org design, and conflict resolution. It had a seat at the table, always.
3. Don’t Under-Resource People Programs
   • Investments were made in DEI, employee engagement surveys, L&D, and mental wellness—essential to scaling a people-first organization.
4. Don’t Overlook the Link Between Culture and Retention (and Performance)
   • In high-churn SaaS environments, culture was your edge in retaining top talent. HR enabled that stickiness through proactive engagement.
5. Don’t Separate GTM Culture from Internal Culture
   • The way Conversica went to market—direct, transparent, high-accountability—was mirrored internally. HR ensured this cultural alignment.
6. Don’t Delegate Culture to HR Alone
   • While HR operationalized the people agenda, the CEO and executive team were the primary culture carriers. You lived it, modeled it, and demanded it.

Our HR philosophy transformed the function from an overhead cost center into a core engine of culture, performance, and competitive advantage.

Finance “Dos”

1. Do Operate as a Strategic Partner, Not Just a Reporter
   • Finance worked hand-in-hand with Sales, Marketing, Product, and the CEO to guide decision-making—not just close books or run forecasts.
2. Do Emphasize Forecasting Accuracy
   • Finance was known for its high forecasting precision, enabling agility while preserving confidence with the board and investors.
3. Do Tie MBOs to Financial Outcomes
   • Departments had measurable outcomes aligned to budget targets and ROI metrics, creating company-wide financial literacy and accountability.
4. Do Enable Flexibility Through Scenario Planning
   • Budgets weren’t static—Finance led dynamic scenario modeling, helping the company navigate shifting economic and revenue realities.
5. Do Support GTM Strategy with Data
   • Finance helped evaluate over 400 metrics: e.g. ROI, CAC, payback, and pipeline metrics, ensuring that GTM investments were efficient and targeted.
6. Do Prioritize Clear, Consistent Reporting
   • Execs and board members had consistent visibility into financial performance and levers—making Finance a cornerstone of transparency.
     

Finance “Don’ts”

1. Don’t Operate in Isolation
   • Finance was most effective when embedded with functional teams. Siloed financial planning led to disconnects in execution.
2. Don’t Let Growth Outpace Financial Discipline
   • Especially post-2022, unchecked growth initiatives were reined in with tighter financial oversight.
3. Don’t Delay Course Correction
   • Timely reaction to forecast variance was a norm—waiting too long to adjust plans was not acceptable.
4. Don’t Build Bureaucracy
   • The lean structure avoided red tape and empowered faster decisions.
5. Don’t Treat All Spend Equally
   • Value-based budgeting ensured cuts or investments were made strategically, not uniformly.
6. Don’t Allow MBOs Without Financial Anchors
   • Goals were expected to align with ROI or cost-efficiency—no standalone targets.
7. Don’t Under-Communicate in a Crisis
   • When conditions worsened, Finance occasionally under-communicated risks or challenges, creating lag in cross-functional alignment. This became a clear lesson: transparency must scale with uncertainty.
     

Finance is more than numbers—it’s narrative, discipline, and foresight. At Conversica, we built a model that could flex with market swings and support strategic bets. But we also learned that financial strategy means nothing if it’s not communicated. Silence during tough times erodes trust. The best finance leaders don’t just report outcomes—they shape understanding, fuel decisions, and bring clarity when the road gets foggy.

International Operations “Dos”

1. Do Make Bold Calls When Conditions Shift
   • In April 2020, Conversica decisively shut down international offices (LATAM & EMEA) to protect runway and focus resources amid the COVID downturn.
2. Do Pivot to Strategic Partner-Driven Models
   • Rather than rebuilding in-region operations, Conversica pursued a partner-first model in LATAM, EMEA, and APAC—leveraging local market knowledge without direct overhead.
3. Do Maintain Global Reach Through Partnerships
   • Strategic partner placements allowed Conversica to retain a global footprint and pursue international opportunities without re-investing in physical presence.
4. Do Focus on Enablement Over Expansion
   • The emphasis shifted from headcount to partner enablement—training, messaging, and co-selling supported performance without internal scale.
5. Do Localize Selectively
   • With limited resources, localization was prioritized for key markets and use cases, avoiding overextension while still supporting core revenue paths.
     

International Operations “Don’ts”

1. Don’t Spread Too Thin
   • The pre-COVID model had risked overextending Conversica’s operational focus. The post-2020 approach emphasized depth over breadth. Two lead partners in each region (NA, LATAM, EMEA, APAC). One Global SI (e.g. Deloitte).
2. Don’t Expect One-Size-Fits-All from Partners
   • Regional partners needed tailored onboarding and market-specific support—copy-pasting US playbooks often failed to gain traction.
3. Don’t Neglect Strategic Oversight
   • Without direct oversight, partner-driven models could drift. Success required ongoing engagement and governance from Conversica HQ.
4. Don’t Assume Brand Awareness Travels Automatically
   • In many international markets, Conversica lacked the awareness it had in the U.S.—requiring partners to double as evangelists, not just resellers.
5. Don’t Under-Invest in Partner Success
   • The early partner model struggled where enablement or support lagged. Success in LATAM, EMEA, and APAC was correlated with dedicated partner management.
     

This pivot to a lean international model preserved Conversica’s global ambitions while staying fiscally disciplined—a move that balanced ambition with pragmatism during uncertain times. 

Corporate Development “Dos”

1. Do Stay Opportunistic with M&A
   • We evaluated M&A not as a default growth lever, but as a targeted opportunity when it aligned with Conversica’s roadmap, customer needs, or market expansion.
2. Do Integrate Corp Dev into Strategic Planning
   • Corporate Development was tied directly into product strategy, GTM alignment, and partner ecosystem development—ensuring deals weren’t siloed.
3. Do Prioritize Build vs. Buy Rigorously
   • The team consistently applied a build vs. buy lens, balancing engineering velocity, IP value, and integration overhead before pursuing acquisitions.
4. Do Use Strategic Partnerships to Test Adjacencies
   • Before committing capital, partnerships (especially OEMs) were used to validate markets or capabilities, creating a lower-risk path to growth.
5. Do Collaborate Across Executive Functions
   • Corp Dev (internal at first, outside advisor/banker later) engaged Product, Finance, and Sales—ensuring evaluations weren’t theoretical, but grounded in go-to-market and delivery realities.
     

Corporate Development “Don’ts” 

1. Don’t Acquire Without a Clear Integration Plan
   • The team considered acquisitions only with post-deal execution strategies, recognizing that integration defines success.
2. Don’t Chase Market Hype
   • M&A efforts were grounded in strategic need, not external buzz, helping preserve focus and capital.
3. Don’t Overlook Cultural Fit
   • Cultural compatibility was a hard filter in acquisition targets—an important safeguard in preserving Conversica’s execution culture.
4. Don’t Underestimate Internal Alternatives
   • In multiple cases, in-house R&D was more effective than pursuing external deals—especially given strong engineering velocity.
5. Don’t Silo Partner Management
   • Partnerships had to be cross-functional. When managed solely by Corp Dev, efforts risked redundancy or confusion across GTM teams.
6. Don’t Proceed Without Board Alignment
   • Lack of consensus among board members around M&A and Corp Dev strategy ultimately diluted the company’s ability to act on opportunities, undermining internal momentum and creating execution drag.
     

While not a frequent operator, Corporate Development at Conversica played a critical role in shaping market positioning and unlocking strategic growth ideas—especially through rigorous partner testing and disciplined M&A evaluation. 

Board Management “Dos”

1. Do Drive Radical Transparency
   • I embedded board members into the rhythm of the business—inviting them to every QBR, sharing full issue transparency, and encouraging unfiltered access to the executive team.
2. Do Create Structured Engagement
   • Board members weren’t passive—they were given homework assignments and engaged in working committees, turning governance into hands-on contribution.
3. Do Assign Clear Roles
   • Each board member was involved based on expertise (e.g., GTM, product, finance), fostering focused input and mutual respect between the board and operating leaders.
4. Do Foster Consistent Attendance
   • Lead investor Eric Filipek rarely missed a QBR, showing the value of continuity and commitment in governance participation.
5. Do Treat the Board as a Strategic Asset
   • I treated board members like co-architects of strategy, not just oversight bodies—pulling them into key decision-making processes.
6. Do Transition Board Composition Strategically
   • As needs evolved, board seats transitioned (e.g., from founder Ben to Alex Terry to Dave Marod to Andrew McCraith), matching leadership needs with board expertise.
     

Board Management “Don’ts”

1. Don’t Withhold Bad News
   • I leaned into radical honesty—ensuring the board knew everything that was going wrong as well as what was going right.
2. Don’t Treat the Board as a Quarterly Update Body
   • Instead of just quarterly updates, you made the board an active part of the business, deeply familiar with goals, blockers, and metrics.
3. Don’t Avoid Governance Evolution
   • When the time came, I handed over Chair responsibilities to Eric Filipek and passed the CEO seat on the board to my successor—ensuring continuity and clarity.
4. Don’t Rely on Formality Alone
   • I encouraged direct relationships between board members and the exec team—shortening feedback loops and building trust.
5. Don’t Leave Strategy Conflicts Unresolved
   • One challenge was the lack of alignment around M&A/Corp Dev, which became a key friction point and diluted effectiveness in that area.
6. Don’t Allow Passive Participation
   

The expectation was clear: engaged, informed, and accountable board behavior is a requirement, not a nice-to-have.

From October 2019 to April 2025, Conversica underwent a profound transformation—from a single AI use case focus (sales), single vertical (Auto), SMB-focused,  inside sales G2M, to a multi-product, enterprise-grade AI platform with global reach and disciplined go-to-market execution, and the leader in our category. We rebuilt every function, reimagined the product-market fit, weathered macroeconomic shocks, and emerged with a team and culture forged in transparency, urgency, and accountability. What we achieved wasn’t just operational change—it was a redefinition of what Conversica stood for. AI may have been our product, but transformation was our mission—and we led by doing the hard things, the right way.

See “An AI Startup CEO’s Reflection“.