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First Round Capital

Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)

In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems.

Brett BersonhostGraham Morenoguest

May 21, 20261h 4mWatch on YouTube

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Old playbooks vs. AI-era backlash: finding the middle ground
Brett Berson asks whether selling has fundamentally changed in the LLM era. Graham Moreno describes a backlash against cloud-era “playbooks,” especially among newer, product-led companies, but argues the reality is in the middle: structure still matters, while timing and tone of sales involvement has shifted.
- •A wave of “anti-playbook” sentiment has emerged in newer companies with pride in PLG
- •Some founders and teams aim to inject sales as late as possible rather than run rigid processes
- •There can be a negative ethos around the word “sales” in newer, AI-native environments
- •Graham frames the modern reality as neither pure playbook nor pure improvisation
Why structured enterprise rollouts still win over ‘let the market decide’
Graham explains that enterprise success often hinges on change management rather than the technology alone. He contrasts structured rollouts—training, workflow discovery, and ongoing enablement—with approaches that drop multiple tools into an internal marketplace and hope adoption sorts itself out.
- •Enterprises still want vendors to deliver trainings, services, and hands-on partnership
- •Windsurf conducted roadshows across regions to support large rollouts
- •Customers reported many AI vendors didn’t show up in person to drive adoption
- •Organizations that relied on internal marketplaces often saw minimal measurable change months later
- •Being strongly opinionated about best practices helps a vendor become more than a software ‘vending machine’
Enterprise buyers want step-by-step clarity—and trust built over time
Brett asks why enterprises want to be sold this way. Graham emphasizes the difficulty of moving large groups of people and the need for a clear value proposition for training time, plus relationship-building that makes change management stick.
- •Executives know large-scale behavior change is hard and value step-by-step guides
- •Training must justify time away from work with clear near- and mid-term outcomes
- •Ongoing enablement and repeated interactions build trust and adoption
- •Human relationships influence whether teams listen and follow through
- •Longstanding trust explains why large integrators can be so effective
Even in AI-enabled orgs, workflow consistency doesn’t scale without guidance
Graham describes how AI tools have changed his own day-to-day work at Parallel, improving access to internal information and speeding up outputs. But he argues that in large rollouts, teams still need vendor partnership to avoid fragmented workflows and inefficiency at scale.
- •AI tools inside the company can materially change individual productivity and prep
- •Teams naturally develop different usage patterns even within a small group
- •Scaling AI usage across thousands without guidance can create redundancy and inefficiency
- •For large deployments, he’d still prefer vendor help to redesign workflows and drive adoption
‘Squeezing the orange’: selling to engineers and executives in one motion
Graham lays out a model of great enterprise selling that applies pressure from both ends: deep engagement with developers and equally strong executive alignment. He argues sales teams can become a conduit of information across organizational layers, translating feedback both ways.
- •A strong developer motion (community, meetups, DevRel) is critical but insufficient alone
- •Executives face budget pressure and need a narrative tied to outcomes
- •Sales can translate developer realities to CIO/CTO-level stakeholders and vice versa
- •In complex enterprises, vendors can help bridge many layers between engineers and the C-suite
- •The value add can extend beyond product features into organizational insight and alignment
Early force multipliers: partners, enablement, and data instrumentation
Graham explains decisions he pushed for early at Windsurf: investing in partners for delivery capacity, building a rigorous enablement engine, and hiring data support to measure what works. He argues these “too early” investments create a compounding advantage as the org scales.
- •He prioritized hiring world-class partners, enablement, and data roles early
- •Partners enabled credibility and surge capacity for global enterprise rollouts
- •Enablement aimed to make sellers credible on product, competitors, and the broader market
- •Training outcomes were measured and linked to faster field productivity
- •Early programmatic foundations prevented later scrambling at higher scale
Selling to AI-native buyers: always-on communication and compressed cycles
Graham describes AI-native customers as having a dramatically different education curve because many started using tools like ChatGPT early. He notes Parallel’s sales interactions lean heavily on async channels, creating an ongoing narrative that compresses typical enterprise timelines into days.
- •AI-native buyers often start far ahead on basics and want optimization, not introductions
- •Sales becomes iterative: small suggestions, rapid testing, and fast feedback loops
- •Communication shifts toward constant Slack/text exchanges with frequent short syncs
- •The sales process stages may be similar, but the time intervals are much shorter
- •Cycles that might take 6–8 weeks in enterprise can compress into 5–8 business days
Seller profile: fundamentals stay the same, channels and hard skills shift
Brett presses on whether AI-native selling requires a different persona. Graham argues great sellers over-communicate everywhere; what changes is the medium and cadence, not the underlying traits of caring, problem-solving, and customer focus.
- •Great enterprise sellers already practice high-touch communication, just at a different cadence
- •AI-native selling demands comfort living in Slack/text and maintaining constant context
- •He believes companies overcomplicate seller personas; hire smart problem-solvers who care
- •He looks for sincerity and human orientation—“you can’t fake giving a shit”
- •Hard skills and communication style can differ, often tracking younger reps’ tool fluency
‘Showing up’ as differentiation—plus the guitar-lesson story
Graham argues that in many AI categories, top vendors’ tech can be close, so trust and presence become deciding factors. He shares examples of on-site trainings, participation in hackathons, and a memorable story of a rep teaching a champion’s son guitar during COVID as an example of genuine relationship-building beyond process.
- •Build-vs-buy is often less central; preference and trust can dominate selection
- •When product parity is close, customers choose vendors who reliably show up to help
- •High-touch actions include on-sites, trainings, and engaging around team milestones
- •Investing effort can be paired with clear expectations about access and mutual commitment
- •A standout relationship example involved a rep informally teaching guitar lessons over Zoom
Process without handcuffs: raising the floor without capping the ceiling
Brett asks what should be standardized versus left to individual judgment. Graham describes a philosophy of simple, measurable stages with a few required checkpoints, designed to create clarity and predictability while preserving room for exceptional, creative customer work.
- •Leadership goal: make the process measurable and predictable while keeping flexibility
- •Keep stages simple, with a small number of required “gates” to advance
- •Use process to create clarity about what to do next, not to dictate every action
- •Encourage autonomy: closest-to-customer judgment is often better than leadership’s
- •Hire people expected to outperform leaders in their specific roles and empower them to act
Scaling trade-offs: predictability vs. ‘artists throwing paint’
Graham explains why a team of highly talented but unstructured “artists” can make forecasting and coaching difficult at scale. He argues for a system that makes solid performance repeatable while still allowing high performers to experiment and set new patterns for the org.
- •Varied selling styles can create a “kaleidoscope” that’s hard to forecast across large teams
- •A clear baseline enables non-confrontational coaching using shared metrics
- •A high floor allows diligent reps to be consistently successful even without unusual flair
- •Too much rigor can attract only process-seeking profiles and squeeze out creativity
- •The aim is a system that supports many reps while still celebrating unusual, high-impact moves
Three pillars of GTM leadership: revenue, people development, and cross-functional alignment
Graham defines excellence in leading go-to-market as driving predictable revenue, investing deeply in talent development, and building alignment to reduce friction across the company. He emphasizes expansion and post-close success as central to revenue, and argues enablement is also a cultural engine.
- •Revenue leadership includes net new logos plus programmatic expansion after the first deal
- •Deployment planning should start early: kickoff dates and clear 30/90-day milestones
- •He believes many orgs have shifted away from development, which harms careers and outcomes
- •Enablement should include leaders’ development, not just SDRs/AEs
- •Cross-functional alignment (marketing, engineering, legal, finance) prevents friction and “fences around sales”
Designing peer relationships: 80% aligned, productive conflict, and enablement as culture
Graham argues leadership teams move faster when they share foundational alignment and trust, leaving a smaller portion for healthy debate. He discusses trade-offs of too much agreement versus combative cultures, and describes enablement programs like boot camps as shared touchstones that create pride and common language.
- •He prefers leadership teams that are broadly aligned, with space for debate without politics
- •Escalations should be rare; peers should resolve issues directly without ego
- •Too much agreement risks losing valuable dissent; trust enables productive conflict
- •Enablement can create shared identity through onboarding, testing, and cohort experiences
- •Boot camps and competitions can make excellence feel fun rather than drudgery
AI and enablement: deeper practice, broader competitive landscape, and funnel instrumentation
The conversation turns to how AI changes enablement and what world-class selling requires now. Graham warns against sellers relying on bots instead of learning judgment for complex enterprise dynamics, while also highlighting AI’s potential for simulation and skill-building; he then outlines selling against direct and implied competitors and explains detailed funnel instrumentation from targeting to close.
- •For complex enterprise sales, organizational politics and change management can’t be outsourced to an LLM
- •AI can enable deeper practice through simulation and complex scenario rehearsal
- •Sellers increasingly must understand a broader ecosystem beyond direct competitors
- •Customers need help simplifying an exploding tool landscape and tying systems together
- •He describes instrumenting the funnel from targeting (stage zero) through scope and close with conversion and cycle-time metrics to create a coaching ‘heat map’
Org design calls: post-sales reporting, outsized commissions, and planning horizons in hypergrowth
Graham argues post-sales should report to a single revenue leader to preserve clarity and accountability across the customer lifecycle. He then makes a case for strong commission accelerators to attract competitive reps and intensify performance, before closing with how a GTM leader should phase in process, forecast rigor, and capacity planning, plus what a productive week looks like at scale.
- •He believes GTM direction should come from one accountable leader; split pillars create tension
- •Post-sales should roll up to the revenue leader to prevent handoff dysfunction and misalignment
- •Healthy commission upside attracts a different rep profile and increases competitive intensity
- •He describes a pivotal moment of stress before an acquisition and pride in outcomes for the team
- •On planning: introduce process gradually, build forecasting and instrumentation, then spend significant time 3–6 months out while continuing heavy recruiting and high-leverage 1:1s

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