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Challenges/TalentReach/General/ Mid-Market Account Executive Challenge — Selling the Future of Smart Security

Mid-Market Account Executive Challenge — Selling the Future of Smart Security

Sell company's value proposition to a multi-stakeholder account

B2B Sales
Account Management
Multi-Stakeholder Selling
ROI, Commercial Real Estate
Estimated Time:
30 minutes
Difficulty:Intermediate
Status:Not started
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What You'll Be Doing

Scenario — "Closing the High-Rise Deal":

Company's AI platform turns passive security cameras into proactive monitoring tools. Your prospect: Skyline Properties, a regional commercial real estate group managing 25 high-rise buildings.

They've expressed interest after hearing how the company reduced false alarms by 40% for another client.

Here's what you know:

  • The Security Director wants fewer manual checks and faster incident response
  • The CFO wants ROI within 6 months, with clear productivity metrics
  • The IT Manager is worried about data privacy and integration with existing camera systems

Your Task:

Design and present your sales approach and messaging strategy for this deal. You don't need to deliver a full pitch deck — just explain your thought process and how you'd run the conversation.

Record a video walking us through your approach, and submit two written documents outlining your discovery strategy and ROI/objection handling plan.

What You'll Accomplish

Navigate complex multi-stakeholder sales processes

Tailor value propositions to different buyer personas

Build ROI-based business cases

Handle technical and financial objections

Create urgency without overselling

How Your Work Will Be Scored

Value-Based Selling & Discovery — 40% Stakeholder Management — 30% Communication & Presence — 20% AI Usage Transparency — 10%

What to Submit

Discovery & Stakeholder Map

Document · 1 page maxRequired

Format: .pdf, .doc, .docx, .rtf, .txt, .md

Outline how you'd approach your first 1-2 calls with Skyline Properties:

Key Discovery Questions

  • What questions would you ask each role (Security Director, CFO, IT Manager)?
  • How would you uncover their specific pain points and priorities?

Qualification Signals

  • What would you listen for to qualify the opportunity?
  • How would you identify buying signals or internal champions?

Connecting Pain to Value

  • Focus on learning before selling
  • Show how you'd connect their pain points to Company's value proposition

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ROI & Objection Handling Plan

Document · 1 page maxRequired

Format: .pdf, .doc, .docx, .rtf, .txt, .md

Summarize your strategy for justifying the purchase and handling objections:

ROI Metrics

  • What metrics would you use to justify the purchase? (e.g., reduced guard hours, faster investigations)
  • How would you quantify the value for the CFO's 6-month ROI requirement?

Objection Handling

  • Identify three likely objections (consider: integration, ROI, data security concerns)
  • How would you address each with data or case examples?

Building Urgency

  • How would you reinforce urgency without over-selling?
  • Think practical and conversational — not scripted

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Video Recording

Video · 7-10 minRequired

Format: .mp4, .mov, .webm

Record a continuous, single-take video that includes all three components:

1. Introduction (1-2 minutes) Share one example of a time you ran a complex sales cycle — from first call to close — where multiple stakeholders had competing priorities. How did you align them around a shared value or outcome?

2. Traits Assessment (2-3 minutes) Which situation sounds more like where you do your best work — and why?

  • Scenario A — "The Fast Follow-Up" (Execution): You've just finished a great demo with a security director. The follow-up meeting is tomorrow with their CFO, who only cares about ROI and compliance costs. You have less than 24 hours to prepare a crisp recap and updated deck. Would you thrive on crafting that quick, targeted pitch?

  • Scenario B — "The Long Game" (Discovery): A large real estate group isn't ready to buy yet. You'll nurture the relationship, help them calculate potential productivity gains, and build internal champions across IT and Operations over several months. Would this kind of slow, relationship-driven sale energize you more?

There's no right answer — we just want to understand your natural sales rhythm.

3. Challenge Response (3-5 minutes) Walk us through your approach to the Skyline Properties sales scenario.

AI Usage Declaration At the end of your video, please state one of the following:

  • I did not use any AI tools
  • I used AI tools (briefly describe how, including prompts and edits)

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