When you put a group of enablement leaders from companies like Red Hat, Salesforce, IBM, Cato Networks, DocuSign, and SpotOn in a room for half a day, what do you get? An engaging discussion, exceptional ideas, and a lot of positive energy.
That’s exactly what happened at our recent Chicago Enablement Workshop, co-hosted by SBI and Ambition. The session was designed as a working session, not a bunch of conference presentations: we shared SBI research, heard real-world case studies from Ambition, and then crowd-sourced best practices from the group.
Here are the big themes that emerged.
1. Increased friction in today’s buying journey is real—and managers must be prepared to adapt
We opened with SBI’s latest research on buyer friction in today’s market.
Across industries, buyers are dealing with more complexity, more internal stakeholders, and more perceived risk. That creates friction at every stage of the journey:
- We confuse our buyers with too many options and multiple people calling on one account
- It’s harder than ever to get access to the real decision-maker(s)
- Deals stall because the customer can’t align internally
- External factors create uncertainly and risk in any decision.
The bottom line? Status quo feels safer than change.
The group aligned quickly on one point: you can’t solve this with more content alone. You need frontline managers who can help their teams orchestrate better conversations, qualify more sharply, and coach reps through complex buying groups.
That set up our second theme: what we called the “Frontline Sales Manager of the Future.”
These managers look different from the traditional “super rep turned boss.” They:
- Act as force multipliers for the go-to-market strategy
- Use data and AI to proactively decide where to coach and who to lean into
- Spend less time reporting up and more time in meaningful 1:1s, deal reviews, and call coaching
- They become the change agents and orchestrators for the successful use of AI by their teams.
To support that evolution, we walked through SBI’s AI Competency Framework, which gives organizations a way to assess and build the skills they’ll need across the team—from basic AI literacy to designing workflows, coaching with AI insights, and putting the right guardrails in place.
The takeaway: AI isn’t replacing managers; it’s raising the bar on what great management looks like.
2. Coaching platforms as the engine for consistent execution
Next, we heard from Mark McWatters of Ambition, who reinforced the theme of manager as force multiplier by sharing a few real-life case studies.
In each example, frontline managers were already busy. What they lacked was a system and platform to focus their coaching and connect it to the behaviors that matter:
- Clear visibility into the right leading indicators
- Structured, repeatable coaching cadences
- A way to keep reps and managers aligned on goals week over week
Mark showed how customers are using Ambition’s coaching platform to:
- Turn messy data into simple, role-based scorecards
- Guide 1:1s and team huddles around specific skills, deals, and behaviors
- Recognize and celebrate the right activities, not just end-of-quarter outcomes
- Provide analytics and insights into whether coaching is happening, and where it’s being focused across the organization
What resonated with the group was that this isn’t about adding one more tool—it’s about giving managers a simple operating system for running their teams. When coaching is structured, visible, and tied to clear metrics, it stops being “nice to have” and becomes the way the team works.
3. Crowd-sourced best practices from the room
We closed with a highly interactive discussion on some of the hot topics facing the group. Curated from a much longer list of challenges, the group prioritized three topics for discussion and collaboration.
Balancing global consistency with local relevance
Many participants in the room were trying to answer the same question: How do we drive one global go-to-market motion without ignoring regional realities?
The consensus approach was:
- Build a global backbone—core messaging, plays, and templates owned centrally
- Empower regions to customize the “last mile”—local stories, competitive context, and language
- Use SKO plus a virtual, regional cadence across the year to keep messaging and skills alive
- Measure application, not just attendance: Are reps talking about the product? Are they using the pitch in real deals?
Regional executive sponsorship was seen as critical. When regional leaders treat global enablement as “how we sell here,” (and reinforce the message that the program is important) adoption goes up dramatically.
Combating training fatigue in virtual and blended programs
The group was very candid: sellers are overwhelmed and training time is limited. To keep training relevant and embraced by the audience, leaders are:
- Focusing on universally applicable skills tied to active pipeline
- Using a flipped classroom model—content as pre-work, live time for practice, coach and collaborate
- Keeping sessions short and interactive, with no more than 10–20 minutes of “lecture” at a time between activities
- Making everything deal- and scenario-based: “Bring a deal you’re stuck on and we’ll work it live”
- Being willing to say no or postpone sessions when there are too many competing priorities
Gamification and recognition also came up—leaderboards, badges, and shout-outs—especially when they reward application, not just logging in. Make it fun and reward the behaviors and engagement you’re looking for.
Rethinking SKO as a launchpad, not a one-off
Finally, we talked about Sales Kickoffs—what’s changing, and what teams are doing differently this year.
A few patterns emerged:
- SKO is the start of a year-long campaign, not a standalone event
- Teams are running manager-only sessions before and after SKO so managers know exactly what to expect, how to provide support, and where to coach their teams
- Product or initiative champions (pillar owners) are assigned to drive follow-up and reinforcement
- To combat jet lag and burnout, in-person agendas are being designed with more time for activities and peer connection, and less “sit and get”
- Sellers get some choice of breakouts or tracks, while still aligning around a few non-negotiable global objectives
In short: SKO is shifting from a once a year event to being part of an ongoing enablement system.
Where we go from here
If there was one common thread from the Chicago workshop, it’s this:
The future of enablement lives at the intersection of better buyer experiences, stronger frontline management, and thoughtful use of AI.
Events like this only work when participants are willing to share openly, challenge each other, and bring real problems to the table—and this group did exactly that.
If you’d like to learn more about SBI’s research on Buyer Friction and the Manager of the Future, and our AI Competency Framework, or how we partner with platforms like Ambition to operationalize coaching, we’d be happy to continue the conversation.
