Outsource to Outperform 🔥 From Ordinary to Top 1% with Daniel Lee & Kevin Dearlove

Business model & problem Wingman solves

• Real estate agents get “stuck” at capacity: they feel they shouldn’t spend time on admin/database work, but they often can’t budget for full-time staff (frequently because wages cost roughly what they’d earn more—so hiring feels inefficient).
• Wingman addresses this by positioning remote professionals to multiply output (2–3x income) by shifting teams from:
  • prep/admin work
  • toward high-value revenue activities (calls, listings, closing, brand building)

Who the presenters are (and roles)

• Wingman Group owners: Jonathan and Nick
  • They run/own Wingman, providing remote professionals
  • They operate across sales and property management enablement
• Daniel Lee (client of Wingman)
  • Runs Plum Property and Plum Partners
  • Helps agents build brands and run back-end systems
• Kevin Dearlove (client of Wingman)
  • Selling principal running his agency
  • Actively manages both sales and operations

Remote professional talent strategy (quality + fit)

Talent requirements

• Every hire requires a university degree or relevant certificate
• Example qualifications mentioned:
  • A solicitor doing data work
  • Accounting-qualified staff

Compensation/working model

• Remote professionals work full-time
• Start times are aligned to business needs with time-zone flexibility
  • Mentioned: Philippines time difference is ~2–4 hours depending on daylight saving; some overlap exists
• Communication/tools:
  • Zoom / Microsoft Teams
  • Remote staff receive business email accounts
• The model is framed as work-from-home to improve happiness/productivity
  • Example contrast: long commutes to Manila

Key cultural/behavioral emphasis

• Remote professionals are treated as employees, not “robot VAs”
• Wingman emphasizes integration, training, and ongoing involvement
  • not “set and forget”

Playbooks/frameworks & processes described

1) “Golden hours / Platinum hours” operating principle (sales execution)

• Golden hours: the agent’s time making calls (high revenue activity)
• Platinum hours: preparation before calls
  • who to call, what to say, targeted outreach lists
• Remote professionals focus primarily on Platinum-hour preparation, freeing agents for Golden-hour selling

2) Role-based task outsourcing framework (Daniel’s approach)

• Map each role to tasks, then outsource anything that doesn’t require:
  • physical presence
  • one-on-one client communication
• Remote staff support tasks such as:
  • templates
  • data work
  • CRM operations
  • CMA preparation
  • database/email/text/letter sending, etc.

3) Training + integration playbook (Wingman model)

• 3 months of training in Wingman’s academy before placement
• Training topics mentioned:
  • Australian culture
  • real estate sales & property management
  • CRM training
  • documents/agency agreements
• After placement:
  • fine-tuning and ongoing support
  • Wingman stresses post-onboarding involvement

Concrete execution examples (what remote professionals do)

Daniel Lee (Sales lead + listing/sale pipeline support)

Remote professionals used a standardized listing process:

• For each listing:
  • Generate the 100 closest / most similar properties using RP Data + other sources
  • Find owner contact details (phone/email) for those comparable properties
• Outreach via multiple channels:
  • Email (templated, company branded)
  • Text/SMS (templated; only where mobiles exist)
  • Mail letters (templated on letterhead; generated via CRM and sent as PDFs for printing/posting)
  • Possible phone call follow-up
• Core impact:
  • removes time-consuming prospecting/prep from associates/agents
  • improves responsiveness via multi-touch outreach (email + text + mail + calls)

Also noted, remote professionals supported:

• CMA creation
• market reports
• templated monthly database outreach

Kevin Dearlove (Property management operations + lead PM scaling)

• Remote professionals were integrated into the front office/reception for the whole group (example: “Ivory” overseas)
• Reception/phone handling was done by remote staff at first, rather than pushing immediately to PM/sales teams
• Emphasis on data-driven, template-driven property management workflows
• ROI and scaling lead PM capacity:
  • “Great property managers… are hard to come by,” so support staff improves PM throughput and reduces stress

Metrics, KPIs, targets, pricing & ROI signals

Cost & productivity metrics (directly stated)

• Investment: about $500 per week per full-time remote professional
  • includes training academy + fees
• Implied hourly cost: ~$12–$14/hour
• Training timeline: 3 months before placement
• Income outcome claim:
  • remote professionals can enable “2x maybe 3x” income by enabling better actions (calls + listings + sales)

Business scale metrics (case signals)

• Daniel: Wingman used for ~13 remote professionals
• Kevin: agency staff count ~50–60, with growth supported by remote staff
• Jonathan (property management scale):
  • 2,350 properties in ~4.5 years
  • stated: ~150 acquired, rest organic
• Kevin: ~750 properties (rent roll referenced; checks implied but not quantified)

Operational / timeline checkpoints

• Performance progression after remote professional start:
  • Month 1: learning business-specific processes
  • Month 3: typically becomes a full-time asset with fewer/no mistakes

Marketing / sales enablement impacts

• Multi-touch listing-based outreach supports:
  • listing-to-appointment conversion (prospecting comparable property owners)
  • deal flow generation via targeted, timely CRM-driven communications
• Indirectly supports personal brand output by freeing agents from admin burdens (mentioned as part of income multiplication early in the video)

Dos & Don’ts (actionable recommendations)

Dos

• Invest in training and treat the remote professional like a new hire for process learning
• Use a structured onboarding process:
  • discovery session → candidate testing → match selection → Zoom setup → training + fine-tuning → start date
• Integrate remote staff into the team’s communication stack (Microsoft Teams/Zoom) and workflows
• Treat this as a process change (remote work isn’t just a simple swap)

Don’ts

• Don’t hire and expect instant results
  • best practice is to actively lead integration
• Don’t assume remote professionals are all the same—not everyone fits
• Don’t scale expectations too early:
  • Daniel advises evaluating fit around 3 months
  • if it’s not working, reassess; incremental cost over that period is relatively lower than full long-term commitment

Onboarding & selection process (Wingman)

• Discovery session to understand the business problems to solve
• Select 1–3 remote professionals based on:
  • video test
  • English speaking test
  • personality test
• Zoom call between remote professional and agent/leader
• Onboarding team schedules:
  • onboarding date
  • fine-tuning training 1–2 weeks before start
• Wingman commits to ongoing involvement after onboarding

Confidentiality & compliance claims

• Remote staff sign employment agreements with Wingman
• Security/data handling:
  • access routed through an external server in Australia (cannot download locally)
  • Wingman claims security is stronger than many Australian businesses
• Addresses HR/payroll administration concerns as part of Wingman’s value add
• Notes solicitors on remote team/legal safeguards
  • no incidents cited

Addressing commercial sector applicability (high level)

• Wingman indicates the model applies beyond residential:
  • they train broadly across real estate; commercial is supported
  • example provided: ~10% of clients are in commercial
• They emphasize that top performers share similar business unit structures (processes/checklists), with domain differences

CRM systems mentioned

• Sales CRMs:
  • Agent Box
  • PropertyMe (mentioned in Daniel/Kevin context)
• Kevin noted training “on every single CRM you can think of”
• Onboarding/compatibility with the agent’s existing stack is emphasized
• PM integration is repeatedly referenced as a key driver

Sources / presenters mentioned

• Jonathan (Wingman Group owner)
• Nick (Wingman Group owner)
• Daniel Lee (client; Plum Property + Plum Partners)
• Kevin Dearlove (client; selling principal/agency principal; runs office and manages sales/operations)
• Tom (host/moderator referenced throughout; no separate business role stated in subtitles)
• Susan (mentioned in chat/URL prompt; not a presenter)