K

Kick

Automated bookkeeping and tax optimization platform

Founding BDR Manager

Full-TimeUpdated on 10/20/2026
CA$175k - CA$215k+ Meaningful equity
Mid, Senior
Toronto, ON, Canada
HybridFour to five days per week in the downtown Toronto office.
Sales & Account ManagementSales Development Representative

About the job

Requirements
  • Has 4–7 years of experience working on 0-to-1 outbound as a BDR/SDR leader, running an outbound agency, and consistently surpassing targets.
  • Has run cold outbound end to end by building lists, writing sequences, testing messaging, and dialing to reach a repeatable number.
  • Enjoys phone work and is comfortable spending most of the day dialing and working in the inbox.
  • Is detail-oriented and takes messaging, scripting, and brand seriously.
  • Is a hands-on builder who can work without a RevOps or enablement team and set up sequences, clean CRM data, and build lead tables.
  • Uses AI to accelerate research, enrichment, prioritization, routing, and first drafts while knowing what to keep human.
  • Does well in a startup environment with fast feedback, shifting priorities, and visible performance metrics.
  • Is based in or willing to relocate to Toronto.
Responsibilities
  • Own meetings booked with US accounting firms across cold outbound and warm MQL follow-up.
  • Build cold outbound from scratch by selecting target firms, sourcing and enriching lists with AI workflows, writing sequences, and personally dialing alongside account executives until effective approaches are established.
  • Respond quickly to warm intent by running call sprints on new MQLs, webinar attendees, and sign-ups who did not book, converting them into meetings within hours.
  • Ensure campaigns are tied to clear buying signals and use messaging that strengthens the company brand.
  • Build and run the outbound stack, including domain warming, email and call sequences, lead routing, and CRM hygiene, enabling reps to run signal-led campaigns tailored by account tier, buying signal, and problem hypothesis.
  • Build RevOps foundations by reporting on performance, including show rate and conversion split by cold versus warm outreach, source, message, and rep.
  • Prepare account executives for outbound with scripts, objection handling, and a weekly cadence that keeps performance metrics visible.
  • Partner with Growth on outbound plays that generate new MQLs.
Desired Qualifications
  • Experience selling or prospecting to accountants, bookkeepers, or accounting firms.
  • Was one of the first BDRs at a startup and helped write the playbook.
  • Set up outbound infrastructure, including deliverability and domain warming, HubSpot or Apollo sequencing, and Clay.
  • Onboarded or coached other BDRs.

About the company

Kick.co is a fintech platform that helps small business owners, freelancers, and creators manage money with automated bookkeeping, tax-deduction optimization, and cash-back opportunities, using Blue Ridge Bank N.A. as its banking partner. Transactions are connected via users’ debit or credit cards, and the platform automatically categorizes income and expenses to save time and reduce audit risk, with AI guidance and human-assisted support. It stands out by blending automation with human help and community-sourced tax tips, focusing on tax savings and cash back while outsourcing banking. Its goal is to simplify financial management for its users, helping them save time and money through better bookkeeping and ongoing access to tax and cash-back opportunities.

Company Size

51-200

Company Stage

Seed

Total Funding

$12M

Headquarters

Palo Alto, California

Founded

2021

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Simplify's Take

What believers are saying

  • Kick raised $20 million by November 3, 2025, backing product expansion.
  • Agent Builder Club launched August 10, 2026, deepening accountant adoption.
  • Kick says it serves thousands of U.S. businesses, signaling real market traction.

What critics are saying

  • FreshBooks partnership makes revenue concentration dangerous if channel economics deteriorate in 2026.
  • Bookkeeping automation faces Intuit, Xero, and FreshBooks bundling similar workflows quickly.
  • Negative trust issues from 2025 streamer-death investigation still threaten brand credibility.

What makes Kick unique

  • AI-native bookkeeping plus human review targets accountants, not just solo founders.
  • FreshBooks named Kick its official bookkeeping partner on January 7, 2026.
  • Kick’s accountant programs and community agents build distribution inside firm workflows.

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Benefits

  • Paid Vacation
  • Company Equity

Growth & Insights and Company News

Headcount

6 month growth

2%

1 year growth

2%

2 year growth

2%
Medium
Nov 3rd, 2025
Kick has raised $20M to build the accounting firm of the future

Just 12 months since our launch last year, we’re excited to share more than 3,000 businesses have switched over to Kick.

VentureScout
Apr 14th, 2025
Kick - AI-Powered Accounting Software

Done-For-You Era Accounting

PYMNTS
Dec 30th, 2024
Online Bookkeeping Platform Bench Accounting Announces ‘Abrupt’ Shutdown

Canada-based online bookkeeping and tax filing platform Bench Accounting shut down its services and operations as of Friday (Dec. 27).“We regret to inform you that we have shut down Bench services,” the company said in a notice of service closure on its website. “As of December 27, 2024, the Bench platform is no longer accessible.”Bench’s bookkeeping services and tax advisory platform had more than 12,000 small business customers, according to a press release issued by Bench in September.When announcing a Series B-1 funding round in 2018, the company said it aimed to help small business owners and accountants build and grow their companies.In its Friday notice, Bench said customers will receive information about how to access their Bench records by Monday (Dec. 30) and that it recommends that customers contact modern accounting software provider Kick for support with their bookkeeping.“We know this news is abrupt and may cause disruption to our customers, so we’re committed to helping them navigate through the transition,” Bench said in the notice.The notice included a link to a Kick web page that described services to help customers migrate from Bench to Kick, including free Bench migration, daily live Q&As and a free 2024 bookkeeping review. With the code “BENCH,” customers can get 20% off the Kick Plus Plan and free Bench migration.Kick founder Conrad Wadowski wrote in a Friday post on LinkedIn that Kick is moving fast to offer these services so that Bench customers don’t have to start from scratch and so that Kick can “get your financials back in your hands.”“You may have just heard Bench has abruptly closed down,” Wadowski wrote in the post. “If you’re a customer, I can’t imagine the frustration you’re going through

US Connections
Dec 27th, 2024
Bench shuts down, leaving thousands of businesses without access to accounting and tax docs

The notice recommends customers migrate to Kick, a new accounting startup that announced its $9 million seed raise in October 2024 in a round led by OpenAI and General Catalyst.

MamStartup
Oct 28th, 2024
9 mln USD na „automatyzację nudnych rzeczy” w księgowoś...

Założony przez Conrada Wadowskiego startup zebrał 9 mln dolarów w rundzie seed. Pieniądze na automatyzację księgowości wyłożył OpenAI, General Catalyst oraz ponad 50 aniołów biznesu.