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Sales Kickoff

Sales Kickoff is a multi-day event that combines executive framing, keynote inspiration, and hands-on skill-building to shift how a sales team sells and how it spends its time. The arc runs from pre-work grounded in The Challenger Sale (teach, tailor, take control) through mindset-shifting curiosity work using the "I Wonder, What If, Let's Try" process, into applied skill-building on opportunity research, prospecting, and negotiation using tools like SalesHub, PowerBI, and Copilot. Participants practice the Breakthrough Selling Framework (Networking, Consulting, Value, Challenge, Selling) to hunt for growth in underworked accounts, and work through a realistic legacy-customer pricing case study to build negotiation and margin-protection skills. Peer-led Unconference sessions let participants teach each other from real work challenges, and the event closes with time-blocking, regional recaps, and personal commitments that turn what was learned into a concrete plan for the following weeks. Several modules are built around specific scenarios — a Palm Beach opportunity, a Mattson growth push, and a "Legacy Global Foundry" pricing negotiation — and are designed to generalize to any comparable account, opportunity, or negotiation a participant faces.

6 modules · 12 exercises · ~5.5 hrs

What you'll practise

  • Exercise: I wonder, what if, let's try
  • Power (Half) Hour - Opportunity Deep Dive
  • Opportunity Power (Half) Hour - Practice!
  • Power (Half) Hour - Prospecting Demo
  • Prospecting Power (Half) Hour
  • Power Half Hour Prospecting: Write down two insights

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The outline is below. A free account reads the first module in full, gets 5 AI coach messages a day, and 2 custom skill builds — no code, no card. A subscription unlocks the rest — 14 days free to start.

1

Breakthrough Selling

3 exercises · ~25 min

This module is built around Mattson's Sales Kickoff push to find "the next $50M" in growth, focusing on Tier 2 and Tier 3 customers, geo-neutral regions, and cross-region collaboration. Participants learn the Breakthrough Selling Framework???Networking, Consulting, Value, Challenge, and Selling???and apply it by working in regional groups to identify a real Tier 2 or Tier 3 account from that morning's business unit discussions, analyzing it against each element of the framework, and presenting their findings in a 90-second pitch. The scenario centers on Mattson's specific growth targets and account tiers; the underlying framework generalizes to diagnosing and pursuing breakthrough opportunities in any account base.

The Breakthrough Challenge~5 min

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High Performance Selling Framework~5 min

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Exercise: Breakthrough Opportunity Mapping~15 min

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2

Pre-Work: Sales Kickoff

1 exercise · ~15 min

Pre-work for the national Sales Kickoff meeting, built around the Challenger Sale framework. Participants read the Introduction and Chapters 1-3 of "The Challenger Sale" and prepare answers on what to apply, what doesn't fit, and what new habits to try. They also select three stuck or challenging open opportunities from their pipeline and document the decision-maker, actions taken, and blockers for each, and run a weekly time audit of their calendar using a Challenger-based (Teach, Tailor, Take Control) prompt to analyze how they spend their selling time. This generalizes to preparing salespeople to actively apply a new sales methodology to their real pipeline and time management.

Pre-Work~15 min

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3

Sales: Interactive Case Study Exercise

2 exercises · ~80 min

This module uses a case study built around "Legacy Global Foundry," a fictional long-standing customer that is buying fewer tools yet still expects strategic-level pricing, frozen labor rates, and legacy spares discounts. Working in mixed cross-functional groups of field service, sales, and executive participants, teams work through the customer's commercial profile to identify early warning signs of second sourcing, practice how to advance a pricing conversation when a customer threatens to walk away, and propose negotiating boundaries leadership could set for sales. Groups share their conclusions in a facilitated debrief, where common themes and open disagreements are surfaced and turned into concrete next steps. The scenario is specific to this legacy-customer pricing situation, but the underlying skills???spotting margin erosion signals, holding firm in a high-stakes commercial conversation, and defining clear negotiating boundaries???generalize to other legacy-customer or margin-pressure conversations.

Interactive Case Study Workshop~60 min

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Interactive Case Study Workshop: Debrief~20 min

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4

Leadership Introductions

1 exercise · ~5 min

This module covers how senior leaders (CEO, SVP Sales, and other executives) open a Sales Kickoff with a brief personal introduction that sets tone and context for the event. Participants practice delivering a short, focused leadership introduction using the agenda and instructions provided for their specific role.

Leadership Introductions~5 min

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5

Keynote: Curiosity to Challenge (and Change) Your Mindset

5 exercises · ~60 min

This keynote module challenges limiting beliefs that hold salespeople back and introduces curiosity as a tool for shifting mindset and behavior. Participants first examine three specific limiting beliefs ??? the Educator Identity Trap, the Relationship Myth, and the Services Belief Gap ??? using curiosity questions to surface where they may be protecting identity, chasing likability, or doubting the value of their offering. They then learn and apply the "I Wonder, What If, Let's Try" curiosity process (illustrated by Sesame Street's approach to curiosity), moving from individual open questions to partnered "what if" exploration to designing a small real-world experiment. The module closes with participants sharing their experiments aloud and recording two takeaways they can apply the following week.

Limiting Beliefs to challenge~15 min

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Curiosity Process: I wonder, what if, let's try~5 min

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Exercise: I wonder, what if, let's try~20 min

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I wonder, what if, let's try: Share out~10 min

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Recap - Add insights to your own notebook~10 min

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6

Challenger Sales Discussion

2 exercises · ~35 min

This module introduces the Challenger Sale framework and its core idea that top performers teach, tailor, and take control of the sale rather than simply building relationships. Participants first review the five sales rep types and the concept of process over relationship-building, then work in small groups to explain the model in their own words, identify which rep types show up on their team, and share real examples of teaching moments and constructive tension from their own pipelines. The module closes with a lightning round on Challenger behaviors and a personal commitment to one specific tactic to try the following week.

The Challenger Sale: Summary presentation~5 min

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Challenger Group Debrief~30 min

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7

Power Half Hour: Opportunity Deep Dive

5 exercises · ~100 min

This module teaches a structured approach to researching a sales opportunity and planning a high-value conversation with its key decision-maker. Participants learn five critical investigation points for understanding an account (strategic plan alignment, key player identification, funding/initiative mapping, proof stories, and obstacle identification), including advanced moves for unsticking stalled or complex deals with multiple stakeholders. The material is built around real opportunities participants bring from their own pipeline (using SalesHub), and a case study on a Palm Beach kindergarten-readiness deal illustrates how to work a complex, stuck opportunity. Participants apply a Teach, Tailor, Take Control framework: gathering one insight to share, tailoring it to the specific decision-maker, and planning when/where/how to set up the conversation ??? with bonus credit for scheduling it on the spot.

Account/Opportunity Deep Dive - Stakeholder Analysis Intro~15 min

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Power (Half) Hour - Opportunity Deep Dive~20 min

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Opportunity Power (Half) Hour - Practice!~30 min

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Opportunity Power (Half) Hour - Debrief~30 min

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Power Half Hour: Write Down Two Insights~5 min

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8

Unconference

9 exercises · ~160 min

This module has participants design and run their own conference. In small groups, participants pitch a 45-minute breakout session on a topic they think is worth the group's time, drawing from real work challenges like handling budget objections or sharing hard-won lessons from mistakes. The group votes, the top pitches become live breakout sessions, and participants choose which to attend using the "Law of Two Feet" ??? moving freely if a session isn't serving them. The module closes with a share-out of insights from each breakout and a personal commitment to two takeaways to apply the following week.

UnConference Introduction~10 min

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UnConference "Walk and Plan"~30 min

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UnConference Pitches~20 min

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UnConference Voting~5 min

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UnConference Announce Winners~5 min

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Room assignments for breakouts~5 min

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Unconference Sessions~60 min

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Unconference Debrief~20 min

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Unconference: Write down two big insights~5 min

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9

Power Half Hour: Prospecting

4 exercises · ~75 min

This module builds a daily prospecting habit using SalesHub and PowerBI to identify strong sales prospects efficiently. Participants first watch a demonstration of high-quality, efficient prospecting as a 20-30 minute daily practice, then apply the same approach to their own accounts???researching a tier one district (drawn from a lost account in their business plan) to investigate past purchases in math and literacy and identify who to prospect next. Working with a curious, investigator mindset, participants generate a list of tier one prospects and craft a tailored insight for each one, then share takeaways and record two applicable insights for their work.

Power (Half) Hour - Prospecting Demo~15 min

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Prospecting Power (Half) Hour~35 min

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Power Hour Debrief - full group~20 min

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Power Half Hour Prospecting: Write down two insights~5 min

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10

Personal Action Planning: Time Blocking

4 exercises · ~70 min

This module helps participants turn sales kickoff takeaways into a concrete weekly schedule using time blocking. Building on a pre-work time audit, participants review what they learned during the sales meeting (curiosity experiments, Challenger sales behaviors, prospecting and opportunity deep-dive power hours, research for insights, unconference ideas) and block time for these on their calendar for the coming week. Participants then pair up to compare calendars, discuss when they're likely to succeed and where they might struggle, and commit to a homework assignment comparing their planned time use against what actually happened the following week. This module is built around a sales kickoff context; the time-blocking approach generalizes to planning any week around newly learned priorities.

Intro Time Auditing Concept~5 min

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Time Auditing Demo~20 min

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Exercise: Design your ideal week~30 min

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Group-Share out/debrief~15 min

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11

Regional Recap

3 exercises · ~30 min

This module closes out the Sales Kickoff by having participants meet in regional groups to translate what they've learned over the past two days into concrete next steps. Working within their regions, participants reflect on key takeaways and surprises, define individual and team commitments, and agree on how to hold each other accountable. Regions then share out their commitments to the full group, and participants identify follow-up work they want to pursue on their own, with facilitator support, or with others outside the team.

Regional Recap Intro~15 min

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Regional Recap: Breakout~5 min

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Team Share outs~10 min

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12

Sales Kickoff Closing

2 exercises · ~25 min

This closing module ties together the full Sales Kickoff by revisiting the mindsets and skills built throughout the day: the Challenger identity shift (teaching, tailoring, and taking control), moving past the "relationship myth" toward a repeatable process, and staying curious using prompts like "I wonder," "what if," and "let's try." Participants review what they practiced across the kickoff ??? the opportunity deep dive in the CRM, peer-to-peer UnConference learning, tier-one account prospecting using maps, data, and Copilot, and time-blocking to protect these habits ??? and commit as a team to specific next actions from their lists. The module closes with leader remarks on key takeaways and a personal commitment to how each participant will re-engage and go deeper over the next two months.

Facilitator: Recap Goals for the meeting~10 min

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Leader: Closing Thoughts~15 min

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