Portfolio | Professional Resume

My Skills and Projects

AI & Scale

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Applying AI and automation to expand seller capacity, accelerate experimentation, and scale what works without increasing chaos.

Sales Prospecting Agents

Designed and launched an Agent + Human prospecting model that scaled personalized outreach while increasing rep effectiveness and accelerating enterprise pipeline creation.

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Results:

386% increase in follow-up rates
28% increase in call connect rates
$5.5M in Stage 1 ACV influenced

Situation

Enterprise sales teams were inundated with more leads and buying group complexity than they could effectively manage. Reps lacked the capacity to personalize outreach at scale, leading to generic messaging, inconsistent follow-up, and missed engagement opportunities. Leadership sought AI-powered prospecting to increase coverage and speed — but without sacrificing the human judgment critical to enterprise deal-making.

Challenge

The central tension was scale versus authenticity. Full automation risked impersonal, low-trust engagement. Pure human effort limited coverage and personalization. The organization needed a true Agent + Human partnership — one where AI could operate autonomously at scale while preserving the rep's strategic role in high-value conversations.

Solution

I partnered with my team to design and operationalize an Agent + Human prospecting model. AI agents executed hyper-personalized outreach across entire buying groups, tracked engagement signals (opens, clicks, replies, timing), and continuously followed up without manual rep intervention. The breakthrough was intelligent routing: Agents surfaced high-intent prospects directly to reps, complete with contextual engagement data — enabling sellers to call warm contacts who already recognized the brand and messaging. This shifted rep time from chasing cold leads to engaging informed prospects primed for conversation.

Detailed Results

The Agent model drove a 386% increase in follow-up rates by ensuring all enrolled contacts received consistent engagement. Call connect times improved by 28% as reps prioritized prospects already interacting with outreach. The program influenced $5.5M in Stage 1 ACV through agent-driven opportunity creation. Critically, rep adoption remained high because the system enhanced performance — allowing sellers to focus on judgment and closing rather than administrative follow-up.

Key Insight

The most effective AI systems do not replace human sellers — they amplify them. AI should absorb the scale problem while intelligently routing human attention to moments that require judgment, empathy, and strategic thinking. When automation and human expertise are deliberately designed to complement one another, performance accelerates without eroding trust.

Inbound Optimization with AI Prompting

Infused AI-powered prompting into global inbound workflows to dramatically improve personalization, reply rates, and process adherence at scale.

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Results:

49% increase in reply rate
87% increase in personalization
49% decrease in skipped steps

Situation

While a structured inbound follow-up framework was already in place, AI prompting had not yet been embedded into the workflow. Reps had access to relevant prospect and account data, but lacked structured guidance on how to translate that information into highly personalized messaging.

Challenge

Without AI-assisted prompting, reps faced a trade-off between speed and quality. To maintain fast response times, many defaulted to generic messaging. This created a "relevance gap" — outreach was timely, but not sufficiently tailored to the prospect's buying stage, role, or context. As a result, personalization suffered and process steps were frequently skipped under time pressure.

Solution

We designed, tested, and deployed standardized AI prompts tailored to common inbound follow-up scenarios and embedded them directly into global automated sequences. Email steps were automated to reduce friction. Prompts guided reps to quickly generate contextualized, high-quality messaging. Reps could paste AI-assisted outputs directly into sequences and redirect time toward phone and social engagement. This shifted AI from a standalone tool to an embedded workflow accelerator.

Detailed Results

Embedding AI prompting into inbound workflows drove a 49% increase in reply rates while increasing measurable personalization by 87%. At the same time, skipped process steps decreased by 49%, demonstrating improved adherence to defined follow-up standards and reduced workflow friction.

Key Insight

In modern selling environments, prospects expect contextual relevance — not just speed. AI must be embedded directly into workflow design to eliminate the trade-off between efficiency and personalization. When prompting is standardized and integrated, relevance becomes scalable rather than optional.

GTM Execution

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Translating strategy into scalable prospecting motions that align Sales, Marketing, and RevOps around consistent execution.

New Offer Launches

Enabled rapid revenue capture from newly acquired AI products by operationalizing scalable, persona-specific messaging and AI-assisted sales workflows.

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Results:

4 successful product launch integrations
Activated across both existing customer base and net-new accounts
Deployed across all segments and industries

Situation

Over a two-year period, Workday acquired four AI-driven companies: HiredScore, Evisort, Sana, and Paradox. These acquisitions represented significant upsell and cross-sell opportunities across Workday's large global customer base. However, sellers needed to quickly understand and articulate new value propositions across multiple industries, buying groups, and deal cycles.

Challenge

Integrating four specialized AI solutions in rapid succession created "value bloat." Sellers were expected to absorb new product narratives while maintaining fluency in their core offerings. Without structured guidance on positioning, ideal buying groups, and integration into existing sales motions, reps risked increasing stakeholder complexity, slowing deal velocity, and missing immediate revenue opportunities. What should have been a growth accelerator threatened to become a messaging bottleneck.

Solution

For each acquisition, my team built turnkey enablement assets embedded directly into seller workflows. This included: Persona-specific, ready-to-deploy sequences. AI prompts within our proprietary tooling to guide positioning and customization. Clear articulation of ideal buying groups and value narratives. Guidance on how to integrate each product into existing deal strategies. Rather than adding more static materials to sellers' plates, we translated acquisition strategy into executable messaging systems — enabling immediate activation across customer and net-new segments.

Detailed Results

This approach eliminated the typical expertise gap that follows new product acquisitions and accelerated time-to-revenue. Sellers were able to immediately deploy persona-specific, AI-assisted messaging, transforming complex launches into a scalable upsell engine. The result was a unified, consistent sales motion that captured revenue across customer and net-new accounts without the traditional "new product" ramp delay.

Key Insight

New product revenue is lost not because of product awareness, but because of execution friction. Sellers cannot be expected to synthesize large volumes of new information independently. To capture acquisition value quickly, organizations must translate strategy into structured tools, embedded workflows, and clear positioning guidance.

Inbound MQL Follow-Up Framework

Designed and operationalized an automated MQL follow-up system that significantly improved reply rates, reduced unsubscribes, and established scalable inbound execution standards.

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Results:

3x increase in MQL reply rates
8x decrease in MQL unsubscribe rate

Situation

In 2020, Marketing Qualified Leads (MQLs) were distributed through Salesforce reports and manual notifications, requiring reps to claim and follow up independently. This manual handoff created inconsistent speed to lead, limited visibility into follow-up quality, and no accountability around SLAs.

Challenge

Without automation or standardized follow-up processes, reps frequently delayed outreach or relied on generic, bulk messaging. The absence of structured SLAs and messaging governance resulted in low reply rates and unsubscribe levels that exceeded acceptable benchmarks. Leadership lacked both context and insight into inbound conversion performance.

Solution

I built and implemented a comprehensive MQL Follow-Up Framework designed to standardize and scale inbound execution. This included: 300+ product-, language-, and MQL-type-specific sequences. Pre-built, customizable messaging aligned with prospecting best practices. Automated lead routing and sequence triggers. Defined SLAs for speed to lead and follow-up cadence. Performance dashboards to monitor compliance and outcomes. In partnership with internal operations teams, we embedded automation and reporting directly into the workflow, eliminating reliance on manual processes and creating clear accountability.

Detailed Results

The framework drove a 3x increase in MQL reply rates and an 8x reduction in unsubscribe rates, dramatically improving inbound conversion efficiency and brand perception. It also established measurable speed-to-lead standards and ultimately enabled the formation of a dedicated inbound team focused exclusively on MQL engagement and optimization.

Key Insight

Inbound performance does not improve through intention alone. Without automation, defined SLAs, and structured messaging standards, manual follow-up will consistently underperform. Scalable inbound conversion requires systematized workflows, clear accountability, and embedded performance visibility.

RevOps & Sales Effectiveness

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Designing and operating the systems, metrics, and workflows that turn seller activity into predictable, profitable pipeline.

Outreach & Content Supply Chain

Built and governed a scalable sales engagement content supply chain that transformed Outreach from a fragmented tool into a standardized global prospecting engine.

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Results:

185% increase in emails sent
49% increase in calls placed
361% increase in prospects added to sequences

Situation

Following the deployment of Outreach, reps were provided with a limited set of product messaging while simultaneously being asked to sell multiple products across industries and personas. There was no standardized process for sequence creation, usage, reporting, or behavioral expectations. As a result, adoption varied widely and performance was inconsistent across regions.

Challenge

Launching Outreach without governance created a "Wild West" environment that rewarded activity over strategy. Reps faced high cognitive load managing multiple product narratives and personas, leading to inconsistent messaging and fragmented brand presence. Without standardized reporting or sequence management, leadership could not distinguish performance drivers from one-off successes — limiting the organization's ability to scale what worked.

Solution

I designed and implemented an end-to-end intake and governance framework for sequence creation. This included: A structured intake process for new messaging requests. A centralized, brand-aligned sequence library. Clear standards for multi-channel prospecting expectations. Reporting visibility to benchmark performance. To drive global consistency, I led cross-functional enablement sessions across North America and EMEA, positioning Outreach not just as a tool, but as a managed prospecting system embedded into operating rhythms.

Detailed Results

Following the implementation of a consistent operating framework and global enablement, activity scaled dramatically. Emails sent increased by 185%, calls rose by 49%, and prospects added to sequences grew by 361%. More importantly, this activity was driven through standardized, brand-aligned sequences — enabling leadership to benchmark performance and scale best practices across regions.

Key Insight

A sales engagement platform without governance becomes noise at scale. By creating a standardized content supply chain and clear behavioral expectations, organizations can transform activity into consistent, repeatable performance.

Practice & Methodology

Designed and scaled a global AI-assisted prospecting methodology that standardized behaviors, improved accountability, and significantly increased reply rates across a 300+ rep organization.

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Results:

28% increase in global reply rates
Most utilized KPI dashboard across the global revenue organization
Largest spike in AI tool adoption organization-wide

Situation

The global Sales Development organization, composed of 300+ representatives, faced rising quotas, expanding technology stacks, and a mandate to drive greater pipeline output without incremental headcount. Leadership needed improved productivity, consistent operating standards, and better visibility into prospecting performance and practices.

Challenge

Prospecting practices varied significantly across regions and managers. Teams lacked a shared methodology for end-to-end execution. Clear expectations for prospecting behaviors were absent, and a practical framework for manager inspection and coaching was missing. Without consistency or accountability, leadership could not effectively impact performance drivers or scale best practices globally.

Solution

I led the cross-functional team responsible for designing and operationalizing a comprehensive Prospecting Practice & Methodology. This included: A step-by-step AI-enabled prospecting framework outlining how to research accounts, generate messaging, and build personalization. Explicit activity and quality expectations aligned to pipeline outcomes. Clear prompting guidance to ensure effective AI usage. Centralized KPI dashboards consolidating prospecting behavior metrics for manager inspection and coaching. To drive adoption, I personally co-led in-person enablement sessions across 7 global offices, partnering with regional leaders to embed the methodology into frontline management routines. The approach combined behavioral clarity, tooling enablement, and accountability infrastructure — ensuring this was not just training, but an operating system.

Detailed Results

The global rollout drove a 28% increase in reply rates, improving the ability of reps to create early-stage pipeline. The KPI dashboard became the most utilized reporting asset across the revenue organization, embedding consistent inspection into manager cadences. At the same time, the initiative generated the largest spike in AI adoption company-wide, with sustained usage that signaled lasting workflow integration rather than short-term activation.

Key Insight

Providing tools alone does not change behavior. To drive measurable performance improvement, learners must define: Exactly how tools should be used. What "good" looks like operationally. How adoption will be inspected and reinforced. Sustainable performance gains occur when methodology, tooling, and accountability are integrated — not introduced independently.

People Leadership

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Building and leading high-trust teams and cross-functional partnerships that deliver results while sustaining strong culture and accountability.

South US and Canada SDR Teams

Built and led a high-performing SDR team that consistently generated qualified pipeline and exceeded Stage 1+ targets.

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Team Mandate

Drive Stage 1+ pipeline generation that converts into Closed Won deals for Workday through disciplined prospecting, campaign execution, and alignment with marketing and field sales.

Team Details

A centralized team of 12 SDRs based in Salt Lake City, Utah, and Quebec, Canada, operating collaboratively across regional markets.

Highlights

Hired the first SDRs in Canada, expanding coverage into a new geography
Supported eight team members in achieving internal promotions
Designed and executed end-to-end campaigns with Marketing and Field Sales prior to the launch of Sales Engagement tooling

Feedback

"Keaton is a rare blend of project leader, people coach and data wizard and he's a highly valued member of the Workday Team. Over the past two years we've worked together, some of the soft skills I admire most about Keaton are his creativity, passion for people, and ability to listen first, and make thoughtful recommendations based on the task or project at-hand. If you are fortunate to work with Keaton, you will immediately recognize these qualities. I look forward to partnering on many future programs together!" — NA Field Marketing

Global Prospecting Effectiveness Team

Built and led a global team that standardizes and scales AI-driven prospecting practices to maximize seller performance and pipeline impact.

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Team Mandate

The team designs, implements, and scales a unified, AI-enabled prospecting methodology that enhances seller effectiveness and drives measurable pipeline outcomes. We establish standardized frameworks and plays, enable sellers across regions, monitor performance, and continuously refine processes to maintain global alignment and consistent business results.

Team Details

A nine-member team distributed across seven geographic regions, bringing together diverse experience levels and tenures to tackle global prospecting challenges collaboratively.

Highlights

Built the team from the ground up
Maintained zero negative attrition during tenure
Successfully navigated shifting business priorities, leadership transitions, and organizational restructuring

Feedback

"Thank you for all of the efforts that you and your team put forth to help our SDRs. From supporting our Enablement team with current best practices to creating tools like the Prospecting Navigator, the impact that you have on our prospecting efforts is incredible. On top of all the great data and content you provide us, what really stands out to me is how collaborative you are to work with and how thoughtful you are when providing advice and strategy. It is truly a pleasure to work with you on joint projects and I look forward to working with you on many more!!" — NA SDR Enablement

Keaton Robertson

Career Profile

My Skills and Projects

AI & Scale

GTM Execution

RevOps & Sales Effectiveness

People Leadership

Career Journey

SDR

SDR Leadership

Sr. RevOps Analyst

RevOps & GTM Leadership

Career Highlights

Workday

InsideSales.com

Personal Life

DIY Enthusiast

Guerilla Gardener

Trail Runner

Chill Seeker