Super hackathon: Boston recap

What’s a Super Hackathon?

Picture a room buzzing with energy, filled with passionate professionals eager to collaborate and innovate. The Revenue Enablement Society and The Enablement Squad hosted an electrifying "Super Hackathon" event designed for in-person mind-melding and idea sharing. The goal is to bring together the brightest minds in the enablement community to foster collaboration and spark creativity.

For our Boston Hackathon, Peter Ostrow from Forrester shared his expertise on measuring the ROI of enablement initiatives. The session delved into various metrics, the importance of timing, and the nuanced responsibilities of revenue enablement teams. Here’s a recap of the key takeaways:

Measuring ROI: The Foundations

How Are You Measuring Today? Peter kicked off the session by asking a fundamental question: How are you measuring enablement today? The discussion revolved around several critical metrics:

  • Net New Pipeline: Tracking the generation of new opportunities.

  • Account Engagement: Especially via channel partners.

  • Program Completion & Adoption: Monitoring how effectively programs are completed and adopted.

  • Corporate Vision Influence: Assessing the impact of enablement on aligning with the company’s broader goals.

A key focus was on leading indicators—those metrics we know will positively influence lagging KPIs. Concentrating on beta customers can lead to stronger, more predictive outcomes.

Why Measure Enablement? He emphasized the importance of understanding what’s genuinely effective, not just what we assume is working. By measuring, we can pivot strategies and prioritize efforts more effectively.

When to Measure? Peter advised that the best time to measure enablement impact is after key milestones, such as certifications and assessments, particularly those tied to KPIs of interest.

Two Essential Truths

  1. No One Metric Fits All: Enablement spans multiple departments and initiatives, so a single metric will never capture its full impact.

  2. Control What You Can: Focus on metrics that reflect what enablement teams can directly influence, recognizing the causal or corollary relationships at play.

Responsibilities of Revenue Enablement

Peter outlined the multifaceted responsibilities of revenue enablement teams:

  • Sales Talent Management: From hiring and onboarding to ongoing training.

  • Sales Asset Management: Ensuring assets are relevant and effective.

  • Communications and Rep Advocacy: Facilitating open lines of communication through office hours, FAQs, and advisory councils.

  • Sales Methodology: Aligning sales processes with overall company strategy.

The Enablement Model: From Activity to Impact

Peter introduced a model that traces the journey from enablement activity to measurable impact:

  • Activity (CYA): Tracking facilitation hours, certifications, and courses delivered—how much are we doing?

  • Output (Quality): Evaluating how well enablement activities are being executed. For instance, did the training help sellers move closer to their quotas? Were the sessions worth the time away from clients?

  • Output (Adoption): Measuring the frequency of use—how often are these tools and practices being adopted?

  • Impact Metrics: The ultimate goal is to understand what behavioral changes in account executives lead to tangible results. Are we giving sellers more time to engage with customers? Are we boosting productivity?

One striking statistic Peter shared was that only 26% of sellers’ time is spent on core customer-facing activities, highlighting the critical need for effective enablement.

Q&A Highlights

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Q&A Highlights 💡

The Q&A session with Peter Ostrow provided a wealth of practical advice, touching on everything from organizational humility to the evolving role of enablement. Here are some key takeaways:

1. Humility in Onboarding

Peter emphasized that the best organizations recognize the importance of not rushing new sellers into the field immediately after onboarding. Instead, they exercise patience, understanding that transitioning from training to fieldwork requires time and continued support.

2. Sourcing the Right Talent

One of the critical responsibilities of enablement is ensuring that HR is bringing in the right "raw materials"—the right talent that fits the organization’s needs. This alignment is essential to set sellers up for success from the very beginning.

3. The Power of Patience

High-performing organizations often require up to 129% more field observations before they formally certify sellers. Peter's advice? Be patient. This investment in thorough observation and certification pays off in the long run by ensuring that sellers are truly ready for the field.

4. In-Person Training Preferences

Despite the rise of digital learning tools, in-person training remains highly valued, never dropping below fifth place in preferred training methods. This insight underscores the enduring importance of face-to-face interaction in skill development.

5. Dos and Don’ts for Enablement Success

Peter shared a few important dos and don’ts for those in enablement roles:

  • Don’t: Avoid expecting bonuses merely for hard work or overall company success. Also, don’t waste energy on complaints—focus on action instead.

  • Do: Highlight the time enablement gives back to sellers and the tangible improvements made. Secure endorsements from sellers to validate your efforts.

6. Tools as Enablers, Not the Focus

Peter reminded attendees that tools are not the end goal but rather a means to achieve the desired outcomes. It’s essential to keep the focus on the projects and objectives that these tools are meant to support.

7. Help Desk Evolution

A low-tech help desk can be an effective starting point for handling questions quickly and accurately. However, Peter suggested that organizations should progress towards using bots and AI to enhance efficiency. Regardless of the technology used, it’s crucial to establish a Service Level Agreement (SLA) for response times, even if the answer isn’t immediately available.

8. Field Sales Coaches: A New Approach to Support

Finally, Peter highlighted the role of enablement field sales coaches. He likened them to helpful aunts and uncles who provide supportive and kind coaching, allowing managers to reserve "tough love" for when it's really needed. This approach fosters a more positive and effective coaching environment.


Overarching Theme: Measuring for Guidance and Success

The central theme of Peter Ostrow's enablement session was the importance of measuring for guidance and success. This approach is critical for aligning sales efforts across different roles, tenure, and seller types, ensuring that enablement strategies are both effective and relevant.

Sales Alignment: Tailoring Enablement to Diverse Needs

Sales alignment involves working closely with various types of sellers—whether they focus on installing new solutions, driving net new business, or serving in roles like Account Executives (AEs), Business Development Representatives (BDRs), Account Managers (AMs), or sales leaders. The key is to ensure that enablement efforts are aligned with the unique needs of each role.

Lanes of Training:

  • Sales Training: Covering sales methodologies and rules of engagement.

  • Product Training: Ensuring sellers understand what they are selling.

  • Customer-Facing Training: Equipping sellers with the assets and resources they need to engage with customers effectively.

  • People Training: Focusing on soft skills development and career growth.

Understanding what a BDR needs versus what an AE or a CSM/AM needs is crucial. Each role has distinct requirements, and successful enablement must reflect this diversity.

Balancing Quantitative and Qualitative Metrics

Peter emphasized the importance of balancing quantitative data with qualitative insights. While hard numbers are critical, understanding intangibles—such as willingness to learn, coachability, and energy—provides a fuller picture of a seller’s potential. This nuanced approach has proven invaluable to managers when assessing talent.

To aid hiring managers, Peter suggested using a scorecard with phrases that signal positive or negative attributes. For example, at EZ Cater, hiring criteria focus on intelligence, communication, grit, and fit—critical traits that align with the organization’s needs.

Skill vs. Will:

  • Do you have the tools to evaluate and advance both skill and will?

  • Completion rates may be irrelevant if they’re not impacting the right KPIs.

What KPIs Matter to Sales?

The session highlighted that the most time-consuming and comprehensive training activities—such as videos, recordings, and pitches—are often the most impactful. It’s essential to ensure that enablement efforts are tailored to where AEs are in their process, whether they’re selling, renewing, or pursuing other goals. Clean and accurate data is vital for this alignment.

Metrics for Different Stages:

  • For New Hires: Focus on metrics like time to first deal and pipeline conversation metrics.

  • For Seasoned Reps: Consider the time taken on training to find the sweet spot that provides the most guidance.

Creating Sales Alignment: Pillars for Success

Peter outlined several pillars essential to creating strong sales alignment through enablement:

  1. Know Your Audience: It helps if you’ve been in the audience’s role. If not, develop a deep understanding by spending time with them.

  2. Understand the Audience’s Problems: A CRO thinks about problems differently than a BDR. Guiding conversations to identify gaps that reveal these problems is crucial.

  3. Communicate While Solving Problems: Continuous feedback loops, buying committees for tools, and regular check-ins help ensure that you’re on the right track.

  4. Be Relevant: Tailor your enablement efforts to the specific needs of different roles, ensuring practical applicability.

Marketing Alignment: Leveraging Collateral and Building an Internal Brand

Aligning marketing efforts with sales enablement is vital for driving success. Collaboration with product marketing, understanding what assets high-performing reps use, and ensuring content is aligned with sales outcomes are key components.

  • Collateral Use: Focus on how marketing materials are used and how they can be better leveraged for sales success.

  • SEO and Content Strategy: Ensure that SEO strategies align with the topics your team needs to address, enabling them to speak knowledgeably about key issues.

Peter cautioned against falling into the trap of measuring tool adoption alone, which can be as misleading as measuring collateral usage without understanding its impact.

Launching Products: Effective Enablement Strategies

When launching a new product, it’s important to ask:

  • Can the rep answer basic questions about the product?

  • Does the product build pipeline?

  • Are people talking about it on calls?

Ensure that launches are addressed both at the macro level (company-wide) and the micro level (individual teams). Tailor training to the level of interest and use insights from the field, such as a lack of technical wins, to inform future product and enablement development.

By focusing on these strategies, Peter emphasized that enablement teams can provide the guidance and support needed to drive sales success, ensuring alignment across the organization and delivering measurable results.

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Super hackathon: Denver recap