Full-Time

Go-To-Market Associate

Wing Assistant

Wing Assistant

1,001-5,000 employees

Subscription-based virtual assistant services for businesses

Compensation Overview

$1.2k - $2.5k/mo

Calgary, AB, Canada

Remote

Remote within Canada.

Category
Sales & Account Management (1)
Required Skills
Sales
Lead Generation
Cold Calling

Get referred to Wing Assistant

See people who can refer or advise you

Requirements
  • 1 to 4+ years in sales, appointment setting, cold calling, recruiting, staffing, lead generation, outbound marketing, growth, or a comparable role.
  • A real interest in go-to-market strategy, pipeline generation, and B2B growth.
  • Proven background in prospecting, cold calling, appointment setting, or high-volume outbound outreach.
  • Strong written and verbal communication; you can get to the point and make it compelling.
  • Comfort reaching out to companies that may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce solutions before.
  • Strong research skills and the ability to turn hiring signals into relevant outbound messaging.
  • Strong organization and the resilience to keep going when a day does not go your way.
  • The drive that comes from chasing clear goals, activity metrics, and booked meeting targets.
  • The ability to run your own desk while still collaborating well across teams.
  • A genuine eagerness to learn the product, the market, and the craft of go-to-market execution quickly.
Desired Qualifications
  • Exposure to staffing companies, recruiting firms, BPOs, outsourcing companies, virtual assistant companies, digital agent companies, or high-ticket professional services organizations.
  • Familiarity with CRM and sales engagement tools such as HubSpot, Salesforce, Outreach, Salesloft, Apollo, Instantly, Clay, Close, or LinkedIn Sales Navigator.
  • Familiarity with auto dialers, power dialers, cold calling workflows, and high-volume outbound systems.
  • Experience prospecting into founders, executives, operations leaders, HR leaders, recruiting teams, customer support leaders, sales leaders, or department heads.
  • Awareness of business support workflows such as executive assistance, admin support, sales support, customer support, recruiting coordination, inbox/calendar management, and back-office operations.

Wing Assistant provides virtual assistant services for businesses, offering dedicated virtual assistants that work remotely on a full-time or part-time basis through a subscription model. Clients hire VAs who handle administrative tasks such as invoicing, payment tracking, and expense recording, while gaining complimentary access to the Wing Task Workspace App for communication, task management, file sharing, and screen recording. The service works by assigning a dedicated VA and, if needed, a Customer Success Manager plus thorough training for assistants to ensure consistent quality. This differentiates Wing Assistant through a strong emphasis on customer support and investment in VA training, with pricing tied to service level and hours required. The company’s goal is to help businesses run more efficiently by providing reliable, scalable administrative support via licensed remote assistants.

Company Size

1,001-5,000

Company Stage

Seed

Total Funding

$2.2M

Headquarters

Irvine, California

Founded

2018

Get referred to Wing Assistant

See people who can refer or advise you

Simplify Jobs

Simplify's Take

What believers are saying

  • Achieved $1.3M GSV in under one year post-launch, demonstrating strong market demand.
  • Founder team from UCI with pandemic-driven pivot attracted $2.1M seed from tier-one VCs.
  • Subscription model with $699–$7,999/month pricing captures diverse customer segments profitably.

What critics are saying

  • AI automation platforms eliminate invoicing and expense tracking demand within 12–24 months.
  • Agentic AI founders render human VAs obsolete as startups adopt zero-cost automation.
  • Four-year funding drought since 2022 prevents AI integration while VC-backed competitors scale.
  • BELAY and Time Etc capture vertical markets through superior domain expertise and budgets.
  • Philippine VA providers undercut pricing by 50–70%, compressing margins or losing clients.

What makes Wing Assistant unique

  • Managed marketplace model pairs VAs with dedicated CSMs and Wing Workspace App.
  • 25+ specialized plans across sales, marketing, healthcare, real estate, e-commerce.
  • Software-augmented VA service with expert-level assistants managing projects independently.

Help us improve and share your feedback! Did you find this helpful?

Benefits

Performance Bonus

Job Security

Paid Training

Inclusive Culture

Upskilling Opportunities

Remote Work Options

Exceptionally Supportive Team

Opportunities for Career Growth

Company Social Events

Holiday & Overtime Pay

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
FinSMEs
Mar 31st, 2022
Wing Assistant Raises $2.1M In Seed Funding

Wing Assistant, an Irvine, Calif. – based platform enabling companies to find remote talent for recurring work, raised $2.1m in seed funding. Backers included Surface Ventures, Brookstone Venture Capitaland UC BerkeleySkyDeck as well as angel investors. Co-founded by Karan Kanwar, CEO, Martin Gomez, COO, Saideep Gupta, CTO, and Roland Polzin, CMO, Wing Assistant provides business [] The post Wing Assistant Raises $2.1M in Seed Funding appeared first on FinSMEs.

Robotics and Automation News
Nov 5th, 2020
Wing Assistant partners with Kiwibot

Wing AI is partnering with KiwiBot to develop robotic delivery services.

Robotics and Automation News
Aug 18th, 2020
Wing Assistant is developing robotic delivery services

Wing AI is partnering with KiwiBot to develop robotic delivery services.