Sales Executive (IT Solution)

Weekday AI · Mississauga, ON, Canada

Base: Not disclosed
OTE: Not disclosed
Quota attainment: Not disclosed
Posted: 7mo ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 1h agoon Weekday AI's careers page

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The job

What you'd do: Hunt new business selling CCM and print solutions to banks, insurers, healthcare, and large enterprises, plus printing companies and outsourced print providers. Cold calling and networking; handoff to delivery after close.
Who you'd sell to: Still reading the posting. Check back within the hour.
Where deals come from: Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: No pay listed at all.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle.
Pipeline: Mostly self-sourced. Great if you like outbound, rough if you don't.
Time on market: Open 228 days. Ask why it's been hard to fill.
Company hiring: 10 sales roles open, hiring at a steady pace.

Red lights

None spotted.

Yellow lights

Open 90+ days. This role has been posted for three months or more. Ask why it's been hard to fill, and whether anyone left it.

Green lights

None spotted.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
This role has been open a while. What's made it hard to fill?
The answer tells you what candidates saw that made them walk.
2.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
3.
What percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
4.
Has the comp plan changed in the last 12 to 18 months? What changed?
A plan that changes every year means the goalposts keep moving.
5.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
6.
Why is this role open? Did someone leave, or is it new?
New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

1.
Can I see the full comp plan in writing, including clawbacks and accelerators?
What's in writing is what gets paid. Read it before you sign.
2.
Can I see the actual comp distribution for the team last year, not just the OTE?
The spread shows what most reps really take home. OTE is just the target.
3.
I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?
Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

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Got an offer from Weekday AI? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Full posting

This role is for one of the Weekday's clients Min Experience: 4 years Location: Toronto, Brampton, Mississauga, USA, Texas JobType: full-time We are looking for a Sales Executive to drive new business, generate leads, and build relationships in the printing and CCM (Customer Communication Management) space. The role focuses on identifying opportunities, connecting with prospects, and helping us grow our presence. Requirements Roles and Responsibilities - Generate new business opportunities through prospecting, cold calling, and networking. - Build and maintain relationships with printing companies, in-plant facilities, and outsourced print providers. - Approach banks, insurance companies, and large organizations that outsource print and CCM work. - Set up appointments and open new accounts; hand over signed clients to the delivery/tech team. - Understand customer needs and present tailored CCM solutions. - Manage pipeline and sales activities using Zoho CRM or similar tools. - Attend trade shows, client meetings, and industry events internationally (USA, Europe, Canada). - Send regular email updates and follow-ups on new opportunities. - Own and achieve/exceed sales targets within assigned territory and accounts. Required Skills: - Experience: 4–6 years in sales of software/IT services/printing solutions/CCM products. - Strong understanding of printing industry, CCM solutions, or document management systems. - Established network with printing companies, in-plants, and outsourced providers. - Proven track record in business development and closing enterprise-level deals. - Ability to engage with BFSI, insurance, healthcare, and large enterprises. - Excellent communication, negotiation, and presentation skills. - Must possess a valid passport and be open to international travel (USA, Europe, Canada). - Self-starter, target-driven, able to work independently as a contractor. - Open to provide previous work references. Exp Required: Minimum 4+ years’ experience in enterprise sales. Skills Sales business development New Business Development it sales IT Solutions it solution selling B2B Sales Hunting

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