In today's competitive eCommerce landscape, decision-makers and senior operators face the constant challenge of aligning their operations for sustainable growth. In a recent conversation with Jonni from Resend, a SaaS company revolutionising how email infrastructure serves developers, we uncovered transformative strategies for tackling retention, operational efficiency, and strategic prioritisation. This article distils those insights into actionable advice to help mid-level eCommerce businesses refine their approach to growth, retention, and operational scaling.
The Power of Retention: Building a Non-Leaky Bucket
Retention is the cornerstone of long-term growth, yet interpreting retention data can often feel murky. Jonni emphasised the critical importance of understanding retention metrics not just as raw numbers but as indicators of deeper, actionable insights.
Why Retention Tables Matter
Visualising retention in cohort tables can reveal patterns that traditional metrics may obscure. For example:
Stabilisation Points: Analysing how churn curves flatten after a specific period (e.g., three months) helps identify when customers who stay are likely to remain long-term.
Leaky Funnels: If retention continues to decline instead of stabilising, it signals broader issues in onboarding, product-market fit, or customer targeting.
Jonni shared how Resend uses an inverted graph of retention tables to visualise churn trends. By spotting patterns, they identified stabilisation within initial months for one product line but persistent declines in another, prompting a strategic reassessment.
Takeaway: Retention metrics, when viewed over time, serve as a diagnostic tool to highlight areas needing improvement - whether that's marketing alignment, onboarding processes, or product value realisation.
Strategic Prioritisation: The Art of Saying No
For eCommerce businesses at the $1M–$10M revenue stage, focusing limited resources on the right opportunities is key. Resend’s method for prioritising their roadmap offers a lesson in balancing ambition with operational reality.
Key Steps in Effective Prioritisation
Democratic Ideation: Encourage input from all team members, regardless of role, to capture diverse perspectives on what the business should build or improve.
Reality Check: Scrutinise the roadmap against historical performance. For example:
Did you achieve last quarter’s goals?
If not, what will change this quarter to ensure progress?
Opportunity Cost Analysis: Assess the ROI of each initiative. Jonni highlighted the importance of measuring not just financial cost but the time and focus required from teams, asking pointedly, "What else could we do with this $500,000?"
By taking a disciplined approach, Resend avoids overextension and ensures that each initiative directly contributes to strategic goals.
Takeaway: A structured roadmap process, anchored by rigorous evaluation, enables businesses to focus on high-impact opportunities while avoiding distractions.
Growth Metrics that Drive Decisions
Metrics are the lifeblood of scaling a business, but knowing which ones to prioritise can be challenging. Resend focuses on two key metrics to align their operations with growth objectives: ARR per headcount and retention cohort trends.
ARR per Headcount
As Jonni explained, this metric is pivotal in assessing scaling efficiency. While burn rate dominates discussions in the early stages of a business, ARR per headcount becomes a better indicator of how effectively a team is being leveraged as the company grows. It aligns hiring decisions with revenue growth, ensuring operational sustainability even as the business expands.
Retention Trends by Cohort
Tracking retention trends by customer segment, instead of relying solely on averages, provides actionable insights:
A cohort with high churn may indicate a misalignment between marketing promises and product experience.
Conversely, cohorts with expanding revenue (e.g., 120% retention) signal successful onboarding and opportunities for upselling.
For instance, Resend identified that a Product Hunt launch cohort had unusually high retention and expansion, which led them to investigate what made this group so sticky compared to others.
Takeaway: Both ARR per headcount and detailed retention analysis offer invaluable insights into business health and scalability.
Leadership in Scaling: Shifting from Operator to Visionary
Jonni’s journey from an individual contributor to a co-founder offers a powerful lesson in leadership evolution. As a founder, there’s a necessary shift from achieving personal wins to enabling others' success. This parallels the shift senior eCommerce operators must make as their teams expand.
Servant Leadership in Practice
One-on-One Connections: Jonni prioritises unstructured, agenda-free one-on-ones with team members to build trust and gather insights that might not surface in group settings.
Empowering Introverts: By creating space for quieter team members to share their thoughts, Resend ensures that valuable insights aren’t overshadowed by more vocal contributors.
Celebrating Wins Creatively: From team dinners to kudos channels, Resend fosters a culture of shared success despite being a fully remote team.
This approach not only enhances team alignment but also builds the relational equity needed to weather challenges.
Takeaway: Effective leadership is less about taking credit and more about creating an environment where others can thrive.
Measuring What Matters: Insights from Retention to Anomalies
Jonni underscored the importance of having data systems in place, even before insights become immediately actionable. Trends often only become meaningful when anomalies occur, making historical data invaluable.
Practical Example: Annotations
Marking key events - such as a new homepage launch or pricing change - on retention and revenue graphs can help connect changes to outcomes. For example, if churn decreases following an onboarding revamp, the annotation validates the impact of that change.
Takeaway: Even if your metrics don’t indicate immediate trends, capturing data over time allows businesses to identify and respond to anomalies when they arise.
Overcoming Remote Work Challenges
Running a distributed team comes with unique challenges, particularly around building relationships and fostering collaboration. At Resend, Jonni prioritises:
Regular Off-Sites: Bi-annual team off-sites provide opportunities for in-depth discussions and personal bonding.
Spontaneous Conversations: Initiating informal chats with team members, especially those outside key daily workflows, helps bridge gaps and uncover hidden insights.
Why Relationships Matter
Strong relationships drive trust, which in turn enhances productivity and team synergy. In Jonni’s words, "You’re under-utilising your team’s potential if you’re not fostering relationships."
Takeaway: Remote work requires intentional efforts to build the relational foundations that drive team success.
Key Takeaways
Retention Tables: Use cohort retention analysis to uncover trends and diagnose issues. A stabilising curve indicates healthy churn, while persistent declines reveal deeper problems.
ARR Per Headcount: This metric measures scaling efficiency and aligns team growth with revenue objectives.
Roadmap Discipline: Regularly review past performance to set realistic goals and prioritise high-impact initiatives. Evaluate opportunity costs rigorously.
Servant Leadership: Build trust through personal connection, empower quieter team members, and celebrate wins in meaningful ways.
Data Maturity: Track metrics over time to identify trends and react to anomalies. Use annotations to connect changes with outcomes.
Remote Work Relationships: Proactively foster connections to enhance team synergy and unlock productivity.
Customer Insights: Investigate why certain customer segments - like a Product Hunt cohort - outperform others, and double down on those learnings.
Conclusion
Scaling a mid-level eCommerce business requires a careful balance of operational discipline, strategic focus, and relational leadership. By prioritising retention, measuring the right growth metrics, and fostering team alignment - even in remote settings - businesses can set the stage for sustainable, long-term success. Jonni’s insights from Resend provide a valuable roadmap for decision-makers looking to scale efficiently while staying attuned to their team's and customers' needs.
By focusing on what truly drives growth and addressing inefficiencies head-on, your business can achieve not just growth, but resilience in an ever-changing market environment.
Source: "Master SaaS metrics that matter: Retention analysis, funding transitions, and growth discipline" - Baremetrics, YouTube, Aug 26, 2025 - https://www.youtube.com/watch?v=w2J1XhggwwM
