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The latest episode of Presales Podcast featured a fascinating conversation with Ben Hills, Founder and CEO of Iris, who shared hard-won insights on scaling presales teams while avoiding the burnout that destroys top performers. Hosted by Jack Cochran and Matthew James, the episode explored the delicate balance between high performance and sustainable work practices in today's AI-enhanced sales environment.
Listen to the full episode now!
From Bottleneck to Breakthrough: Ben's Origin Story
Ben's journey to founding Iris began with a familiar presales pain point—becoming the organizational bottleneck. As Chief Operating Officer at an edtech company experiencing explosive growth, he found himself running between five conference rooms, simultaneously demoing their platform to different university prospects.
"There was one period where we had five conference rooms running concurrent demos with universities, and I would bop between the conference rooms doing the product demo at the same time," Ben recalled. While he loved showcasing solutions, the company's scaling challenge became clear: "You can hire 30 sales reps, but you can't hire people off the street with institutional knowledge."
This experience crystallized a fundamental truth about presales scaling—knowledge transfer, not headcount, is often the real constraint.
Redefining Burnout: It's Not Just About Hours
One of the episode's most valuable insights was Ben's reframing of burnout. Rather than simply equating burnout with long hours, he emphasized the importance of purpose and time boundaries:
"You can have people that work 10 hours a week on tasks that they feel are really insignificant, and they get burned out. On the other side, you can have people who work 80, 90, 100 hours a week that are so motivated by the team, by the mission, by the outcome that they feel more energized than ever."
Two critical factors helped Ben avoid burnout during his intense period:
- Clear connection to impact: Every demo meant another college could celebrate graduates virtually during COVID
- Time-bounded intensity: He knew the extreme workload wouldn't last forever
The Athlete's Approach to Sustainable Performance
Matthew James drew an insightful parallel to athletic training, noting that "spending an hour on it every day for a week is going to be much more effective than spending seven hours at it on Saturday." This consistency principle applies directly to presales work.
Ben expanded on this, identifying context shifting as the most expensive deficit in presales teams. "Pre-sales is one of the few functions that sits cross-functionally between teams," requiring expertise in multiple tools and constant mental transitions between technical details and relationship building.
His solution involves two frameworks:
1. In the Business vs. On the Business Work
- In the business: Client calls, demos, investor meetings
- On the business: Strategic planning, website updates, product roadmap discussions
2. Rocks, Pebbles, Sand Framework
- Rocks: Big quarterly tasks you can plan for
- Pebbles: Predictable weekly activities with some prep work
- Sand: Unexpected fire drills and urgent requests
The Headcount Trap: Why More People Isn't Always Better
When discussing scaling mistakes, Ben highlighted the "mythical man month" problem—the assumption that doubling headcount doubles output. His litmus test for new hires: "If someone started tomorrow, could I hand them a playbook on what to work on?"
Before adding headcount, leaders should ask:
- Do we have documented processes?
- What would this person's 30/60/90-day trajectory look like?
- Are we solving skill gaps or just distributing existing work?
Often, this exercise reveals process inefficiencies that can be solved without additional hires.
AI Tools That Actually Move the Needle
Ben shared practical insights on which AI tools deliver real value versus those that add "layers of obfuscation." His team uses:
- Call transcript analysis to extract product feedback for engineering teams
- Demo automation tools with synthetic data relevant to prospects
- Iris itself for RFP responses (Ben completed one the night before our interview)
- Role-playing tools like Udly for practice scenarios
Notably absent from their success stories: AI SDRs. "My growing thesis is that AI isn't about end-to-end, it's about middle-to-middle," Ben explained. "I'd rather free up account executives' time on follow-up emails and proposals than have some automated AI bot cold call 100,000 people."
Demo Automation Without Losing the Personal Touch
When asked about maintaining personalization in automated processes, Ben outlined three key areas where AI enhances rather than replaces human connection:
- Context aggregation: AI can process discovery calls, understand prospect challenges, and auto-generate relevant demo storyboards
- Technical efficiency: Auto-generating voiceovers eliminates the need for multiple takes
- Synthetic data: Creating prospect-relevant sample data that tells a better story
The Future: AI-to-AI RFP Processes
Looking ahead, Ben envisions a world where AI systems communicate directly through technologies like Model Control Protocol (MCP). Rather than eliminating RFPs entirely, this could streamline the alignment process between buyers and vendors while maintaining the detailed requirements that modern buyers demand.
Embrace AI First, Not AI Curious
Ben's closing advice was powerful: "Everyone who brings AI to their company will be best positioned to get promotions and raises." He distinguished between two mindsets:
- AI curious: Try a tool, find limitations, decide AI is a fad
- AI first: Understand AI will change everything, accept the learning curve, and muscle through initial challenges
Key Takeaways for Presales Leaders
- Burnout prevention starts with purpose: Connect individual work to larger company outcomes and customer impact
- Document before you hire: Build playbooks and processes that enable new hires to operate independently
- Focus on middle-to-middle AI: Look for tools that enhance existing processes rather than end-to-end replacements
- Separate planning from execution: Create distinct time blocks for strategic work versus operational tasks
- Embrace AI proactively: The learning curve is worth the competitive advantage
Ben's journey from overwhelmed solutions engineer to successful founder illustrates that the path to sustainable scaling isn't just about working smarter—it's about building systems that amplify human expertise rather than replace it.
Want to try RFP automation for yourself? Ben offers to run your first RFP for free. Reach out to him at ben@heyiris.ai or connect on LinkedIn. Presales LIVE airs every other Tuesday at 8 AM Pacific, 11 AM Eastern, 4 PM GMT. Join the Presales Collective Slack community at presalescollective.com/slack for updates on future episodes.
