Peter Ostrow

VP, Principal Analyst, Sales Enablement

Forrester Bio

Author Insights


“Would You Buy A Car Without Knowing How To Drive?” And Other Sales Enablement Head-Scratchers From 2020

Peter Ostrow October 13, 2020
If 2020 has taught us anything, it’s that change is exceptionally hard for many people. The best sales enablement teams excel at change management.
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Adoption May Be a Luxury, But Respect Is Essential

Peter Ostrow October 2, 2020
Many sales leaders employ, tolerate, and enable high-maintenance sellers, because such reps yield a final product we value. But is this sustainable?
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Practicing What We Preach: An Inside Look at Forrester’s Sales Advisory Council

Peter Ostrow August 20, 2020
Most B2B organizations invest significant effort in customer feedback via customer advisory boards, but many fail to consider the same kind of insight from their internal sales team. Sales advisory councils represent a valuable opportunity for organizations to collect vital sales feedback on major strategic initiatives and identify any broad sales issues that must be addressed. Forrester’s own council is a textbook definition of how high-performing sales teams leverage a sales advisory council.
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Sales Asset Management: Have You Leveled Up?

Peter Ostrow June 10, 2020
  • Far too many sales asset management (SAM) technology purchases are treated as a project, not a lifestyle
  • The result is disappointed sales enablement leaders who miss the ROI potential of their deployment
  • Organizations that best leverage their SAM environment reap the most long-term benefits
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When Is It OK to Start Making Sales Calls Again?

Peter Ostrow April 6, 2020
  • COVID-19’s full impact is far from known, but its reach is unprecedented
  • B2B interactions have been affected severely by the crisis, leaving sales professionals uncertain about how to proceed
  • We offer a discussion on how to tell whether it’s too soon to sell
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‘Twas the Night Before Year End: A Visit from Sales Enablement

Peter Ostrow December 16, 2019
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Enablement Is the New Black

Peter Ostrow October 2, 2019
  • Organizations frequently think of marketing, sales, service and renewal cycles as independent sets of customer interactions
  • Customers are more likely to purchase and renew when their experience is consistent across all interactions with an organization
  • Sales enablement is making strong headway via competency-driven support, but other customer-facing personas should receive similar enablement
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Five B2C Brands We Love – And Why They Matter in B2B Interactions

Peter Ostrow April 16, 2019
  • As consumers, we have strong preferences for the companies we trust and admire
  • These companies thrive because they focus on customer interactions and treat their buyers with respect and relevance
  • B2B organizations can earn the same loyalty – and economic advantages – by learning from their consumer-driven peers
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Are You a Sales Enabler or a Sales Inflictor?

Peter Ostrow January 18, 2019
  • Sales enablement is a rapidly growing function with a wide variety of definitions and responsibilities
  • Some organizations take a legacy approach to enablement rooted in product-centric learning to inform seller-buyer interactions
  • Best practices in sales enablement favor a more holistic approach to developing role-specific skills, knowledge and process awareness that yields stronger sellers
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Why Do I Keep Hearing, “Play it Again, SAM”?

Peter Ostrow November 6, 2018
  • Sales asset management deployments often fail to meet buyer expectations – why?
  • Too often, shiny object syndrome motivates misguided sales enablement technology purchases
  • Replacing a failing sales technology with a new product isn’t a panacea
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What Is a Sales Manager Enablement Playbook, and Why Should I Have One?

Peter Ostrow September 28, 2018
  • Compared to the reps they lead, first-line sales managers often receive significantly fewer opportunities to develop competencies specific to their role
  • Ad hoc and reactive sales manager enablement leads to inconsistent results and processes that lack scalability and repeatability
  • A lack of effective sales manager enablement drives away high-performing managers and their best reps
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Three Customer Quotes About Sales Enablement That Are “Full Send”

Peter Ostrow September 17, 2018
  • Sales enablement is a challenging blend of art and science that requires an extensive understanding of your internal customer
  • Organizations taking a holistic view of enablement – focusing on building great reps instead of conducting simple knowledge transfer – produce win-win results all around
  • While the research business focuses on teaching and guiding customers, sometimes you can learn a lot from them as well
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The Worst Sales Hiring Mistake I Ever Made

Peter Ostrow September 5, 2018
  • The process of hiring sales reps is often rushed by organizational pressures to fill open positions
  • Making an offer to the “best of the bunch” can result in long-term regret
  • Best practices in sales talent recruitment rely on a rigorous process that emphasizes quality over expediency
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Give a Man a Fish, Teach a Rep to Close a Deal: What Great Sales Coaching Really Looks Like

Peter Ostrow June 29, 2018
  • B2B sales coaching is frequently limited to managers stepping into late-stage opportunities and directly closing the deal
  • This short-term approach hinders enablement efforts to develop sales rep competencies
  • To continuously raise the bar on their overall effectiveness, organizations must instead shorten time to competency for their front-line sellers
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Why Being a Boston Sports Fan Matters at SiriusDecisions Summit

Peter Ostrow April 30, 2018
  • Compared with the reps they lead, first-line sales managers often receive significantly fewer opportunities to develop competencies specific to their role
  • Ad hoc and reactive manager enablement leads to inconsistent results and processes that lack scalability and repeatability
  • A lack of effective sales manager enablement drives high-performing managers and their reps out the door
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Sales Learning and Coaching Technology: Three No-Brainer Outcomes

Peter Ostrow March 30, 2018
  • Sales learning has long been executed manually and repetitively
  • Organizations are seeking ways to more effectively deliver learning to high-performing and Millennial sellers
  • Sales learning and coaching solutions are growing in popularity and influence
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Three Ways to Guarantee a Sales Rep’s First Day Is a Terrible, Horrible, No-Good One

Peter Ostrow February 9, 2018
  • New sales hires are a highly valued commodity, and the imperative to get them selling immediately is understandable
  • Acclimating and orienting salespeople to their new environment requires time, patience and planning
  • Many organizations fail to resist the temptation to throw new hires into the sales equivalent of the deep end of the pool
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Four Success Factors for Featuring an Industry Analyst on Your Webcast

Peter Ostrow January 9, 2018
  • Vendor-sponsored webcasts featuring industry analysts are frequently deployed to bring independent thought leadership into the overall go-to-market strategy
  • Webcasts must be managed as carefully as any other marketing event
  • This blog post includes best practices that will optimize your webcast effectiveness
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I’ve Been Selling a Long Time – Just Leave Me Alone and Let Me Make My Number

Peter Ostrow November 17, 2017
  • Long-time B2B sellers are often resistant to change and argue that if it’s not broken, it doesn’t need fixing
  • Today, organizational and commercial change are almost constant, which creates tension among tenured sales reps who want to stay in their comfort zone
  • Sales enablement must support leaders’ change initiatives by creating a win-win outcome for individual contributors and the company
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The Three Degrees of Guided Selling

Peter Ostrow October 3, 2017
  • Sales playbooks have been around for a long time, and remain relevant for many contemporary sales organizations
  • For more complex and customized selling interactions, guided selling goes beyond playbooks and optimizes sales asset management environments
  • Determining the appropriate degree of guidance for a team is a crucial sales enablement function
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