PEOPLE · LEADERSHIP · BUSINESS GROWTH

Grow people.
Improve how we work.
Deliver results.

I’m Oskar — a team leader, coach, and public speaker. I recruit and develop people, coach emerging leaders, and build repeatable systems that help teams grow. As a public speaker and trainer, I bring clarity to feedback, learning, and team conversations.

I bring a commercial perspective to people development: linking recruitment, coaching, and team effectiveness to business results.

Explore my experience Let’s talk

Tallinn, Estonia · Estonian & English · International experience

People first. Results in view.Leadership · Coaching · Optimization

30+People trained & mentored

28Sales group members in 2024

50+Events hosted since 2017

2×Top-10 rookie teams in Europe

Oskar with a group of colleagues at a formal event

01 / SELECTED WORK

Leadership in practice.

Three examples of how I’ve developed people, built repeatable systems, and helped teams deliver results with less dependence on me.

SOUTHWESTERN ADVANTAGE · 2021–2024

Leading a team while delivering on the front line.

Team coordinationCoachingPrioritization

I led direct sales teams in the UK in 2021, Minnesota in 2022 and 2023, and Nebraska in 2024 while also maintaining my own sales responsibilities.

What I owned: Preparing sales territories, arranging accommodation abroad, running weekly meetings, and mentoring team members in sales and leadership.
Outcome: In the best years, the summer teams generated approximately $400,000 in revenue over three months.
What this demonstrates: Understanding commercial pressures while coaching people, setting expectations, and supporting team effectiveness across international projects.

SOUTHWESTERN ADVANTAGE · 2020–2023

Building systems that support growth.

People developmentRecruitmentWorkflow optimization

My personal sales organization grew from approximately $30,000 in annual revenue in 2020 to around $600,000 in 2023.

What I owned: Developing recruitment, sales, and leadership systems; conducting final-stage interviews and selecting recruits; reviewing recruitment performance weekly with senior leadership; and building automated workflows.
Outcome: 30+ people trained and mentored and 120+ interviews. The group reached 28 members in 2024, starting from two in 2020.
What this demonstrates: Connecting recruitment and leadership development to business growth, with repeatable processes that help people take ownership as the organization scales.

SOUTHWESTERN ADVANTAGE

Building teams that develop their own leaders.

OnboardingFeedbackNew-leader development

I recruited, trained, and led two rookie teams that placed among the top 10 teams in Europe.

What I contributed: Coaching managers to recruit and lead their own teams, with regular conversations to track commitments and support recruitment goals. Developing future leaders and discussing plans to return for future seasons.
Outcome: Two top-10 rookie teams. In a business with low retention, 60–80% of team members wanted to continue working with me. Four became Organizational Leaders and one became a Sales Leader.
What this demonstrates: Developing leaders who can coach others, take decisions, and lead independently. By transferring my methods and building repeatable workflows, I help leadership capability spread across the team.

02 / PUBLIC SPEAKING & TRAINING

From team meetings
to the main stage.

Public speaking is a substantial part of my work: helping people learn, guiding live events, and adapting my communication to the room.

50+Events hosted

EN / ETPublic speaking in English & Estonian

2022–25SWA European Division Speaking Trainer

Oskar speaking into a microphone in front of a seated audience — Speaking at the 2023 Pärnu kickoff.

Training people to communicate

As Southwestern Advantage’s European division public-speaking trainer, I helped develop presentation skills. I have also delivered training in sales, recruitment, and leadership, including sales training for Junior Achievement student companies.

Leading the room

Since 2017, I have hosted awards galas, corporate events, weddings, sports competitions, and auctions in Estonian and English. My venues have ranged from private homes to Unibet Arena; Robotex brought audiences of around 10,000 visitors.

Adapting to the audience

I work with clients on the schedule and ask about the event’s purpose, audience, and background. I pay attention to the mood in the room and adjust my delivery — whether the occasion calls for formality, humour, or clear direction.

What this brings to a team lead role

Experience facilitating meetings, delivering training, and communicating confidently with different audiences — useful foundations for explaining new ways of working and keeping a team engaged.

Read my speaking & hosting profile Oskar The Host on Facebook

03 / HOW I WORK

Develop people.
Build stronger teams.

My experience combines recruitment, leadership coaching, and commercial accountability. I help people take ownership and build teams that can grow.

Develop talent & leaders

Recruitment, coaching, weekly meetings, and developing new leaders. Experience working with Estonian, Latvian, Slovak, Ukrainian, and Georgian students.

Build scalable people practices

Built automated systems and repeatable workflows so the organization could operate without my constant involvement. Combined practical project coordination with developing people who could lead independently.

Connect people to business results

Grew an organization from two to 28 members and developed four Organizational Leaders and one Sales Leader. Experience combines people development with responsibility for commercial performance.

Facilitate learning & engagement

Native Estonian, C2 English and German. Public-speaking trainer for Southwestern Advantage’s European division from 2022 to 2025.

Development focus

I continue to develop my leadership, coaching, and analytical skills, with a focus on understanding what helps people and teams perform.

Questions I’d like to explore with you

What would meaningful progress look like for your team over the next three months?
Which people or leadership challenges most affect the business area’s performance today?
Where would support make the biggest difference: leadership coaching, talent development, team effectiveness, or more scalable ways of working?

04 / EXPERIENCE & BACKGROUND

Commercial experience.
Technical grounding.

2022–2025

Sales Leader

Southwestern Advantage

As an Organizational Field Leader (OFL) and Associate Sales Leader (ASL), led recruitment, training, and leadership development across an international organization. Conducted final-stage interviews and made recruitment selection decisions. Built recruitment relationships through campus engagement and high-school presentations promoting the programme. Reported recruitment performance weekly and reviewed progress with senior leadership.

Coached managers to recruit, build, and lead their own teams. Held regular coaching conversations, tracked commitments, and supported recruitment goals. Built a leadership pipeline through ongoing development and conversations about returning for future seasons. Created automated systems and repeatable workflows so the organization could operate without my constant involvement.

Earned two promotions in the sales-leadership track: the first when group revenue reached $260,000, and the second at $500,000.

2021–2024

Organizational Leader

Southwestern Advantage · UK & US

Prepared and led summer sales projects abroad, coordinating territories, accommodation, weekly meetings, and team mentoring. Balanced personal sales targets with responsibility for the team’s execution.

Managers under my leadership increased their personal revenue by $20,000, with one manager achieving a $60,000 increase. Ranked among the top 10 Organizational Leaders in three of four seasons. Developed team members’ ability to solve problems and work independently.

2018–2025

Sales Representative

Southwestern Advantage

Built a seasonal direct-sales business from the ground up in unfamiliar UK and US markets. Managed prospecting, customer conversations, product demonstrations, and personal performance, working 80 hours a week for 12 weeks each summer.

Personally sold approximately $350,000 in merchandise across eight summers and created 16,000+ sales contacts. My best year reached $86,000 in sales and my best week exceeded $14,000, while leading an 11-person team. Learned to establish trust quickly, understand customer needs, and adapt through self-analysis and feedback.

2019–2021

Direct sales & telephone fundraising

Southwestern Ventures

Represented G4S Estonia in shopping-centre and telephone sales, explaining Nublu detectors to prospective customers and creating 10,000+ sales contacts. Later conducted telephone fundraising for Aitan Eesti, discussing recurring donations from a home office.

Worked across face-to-face and remote channels, adapting communication to different audiences and purposes.

05 / BEYOND WORK

Curious. Active.
Always exploring.

Outside work, I make time for books, podcasts, movement, and discovering new places. My best recent memory was sandboarding in Peru and then snowboarding in Chile one week later.

READING

15+ books a year

Reading is a regular part of my daily routine, diving into different topics from sports endurance to building a culture to autobiographies.

MOVEMENT

Mountains, gym & running

I enjoy snowboarding and strength training, and I’m currently preparing to run a marathon in barefoot shoes.

EXPLORATION

30+ countries visited

I especially loved solo trips in Scotland, Ireland, and South America, alongside many work trips in Europe and the US.

CURIOSITY

Health & biohacking

Testing routines, systems, devices, supplements, practices, and mindsets — from very common to super weird.

06 / LET’S CONNECT

Let’s discuss your team.

I’d welcome a conversation about your team, your goals, and how my recruitment, coaching, and leadership-development experience could help.

o.orglaan@gmail.com+372 5901 0574