Mid-Market Sales Manager

Overview

You're managing a team of 6-8 Account Executives selling Mailchimp into mid-market companies (500-5,000 employees). This is a new org being built from the ground up over the past two years, so you're establishing playbooks, refining the ICP, and developing reps while the GTM motion is still being figured out. You'll carry 1-2 strategic accounts yourself while spending most of your time in deal reviews, pipeline management, and coaching.

Role Snapshot

Company Context

Stage: Public (Intuit acquired Mailchimp in 2021 for $12B)

Size: 1,605 employees

Growth: Building out mid-market segment after years of SMB/self-serve dominance. Heavy platform investment happening now.

Market Position: Market leader in SMB email marketing, but challenger in mid-market where HubSpot, Salesforce Marketing Cloud, and Klaviyo compete hard.

GTM Reality

Pipeline Sources:

• 40% Inbound - Existing SMB customers expanding or upgrading, free trial users hitting limits, brand-driven inbound
• 35% Outbound - Your team prospecting into mid-market accounts, account-based plays in target verticals (e-commerce, SaaS, retail)
• 25% Customer expansion - Upselling existing smaller accounts into enterprise plans

SDR/AE Structure: Your AEs are mostly self-sourcing. There's some SDR support for top-of-funnel, but mid-market motion is still being built, so reps generate 60-70% of their own pipeline.

SE Support: Shared Solutions Engineer pool for technical demos and POCs on larger deals.

Competitive Landscape

Main Competitors: HubSpot (full marketing suite), Klaviyo (e-commerce focused), Salesforce Marketing Cloud (enterprise), Constant Contact (SMB)

How They Differentiate: Mailchimp leans on ease-of-use, AI-powered features, and brand recognition. Mid-market pitch is "enterprise capabilities without enterprise complexity."

Common Objections:

• "We've outgrown Mailchimp" (perception as SMB tool)
• "Too basic compared to HubSpot's CRM integration"
• "Klaviyo is better for e-commerce use cases"

Win Themes: Faster time-to-value, lower total cost of ownership, familiarity (many mid-market buyers used Mailchimp at smaller companies).

What You'll Actually Do

Time Breakdown

Coaching & 1:1s (35%) | Deal Reviews & Forecasting (30%) | Strategic Accounts (20%) | Hiring & Admin (15%)

Key Activities

• Weekly Pipeline Reviews: You're in the weeds with each rep's top 10-15 opportunities. Most deals are stuck in "technical evaluation" or "waiting on procurement." You're helping them identify blockers and multi-thread into economic buyers.

• Ride-Alongs & Deal Coaching: You join 4-6 calls per week - demos, discovery, closing calls. You're teaching consultative selling to reps who may have come from transactional SMB backgrounds. You're also jumping into deals that are stalling.

• Forecast Calls with Leadership: Every Friday you're defending your commit number to Tom (Head of New Business). The mid-market segment is under scrutiny because it's new, so you're constantly pressure-tested on deal progression and close dates.

• Hiring & Onboarding: You're hiring 2-3 new reps in your first year. You're also building onboarding materials because this segment didn't exist 18 months ago - there's no established playbook yet.

• Playing Deals: You personally manage 1-2 strategic accounts (probably $200K+ opportunities) where the customer wants executive involvement or the deal is too complex for a junior rep.

• Cross-Functional Alignment: Lots of meetings with Product, Marketing, and Customer Success figuring out messaging, pricing, and handoff processes for mid-market. The GTM is still being defined.

The Honest Reality

What's Hard

• You're building the plane while flying it: This org is only two years old. Playbooks are rough drafts. Your reps will ask "what's the best practice here?" and you won't always have an answer because it hasn't been figured out yet.

• Mid-market skepticism about Mailchimp: Many prospects see Mailchimp as an SMB tool they used 5 years ago. Your reps (and you) will spend energy repositioning the brand and fighting uphill against "we need something more robust."

• Reps self-sourcing most pipeline: Your team doesn't have dedicated SDR coverage for every account. Reps who can't prospect will struggle, and you'll spend time teaching outbound skills to people who expected inbound-heavy books.

• Longer cycles than expected: Deals that look like 60-day closes turn into 120-180 days. Mid-market buyers involve more stakeholders (IT, Ops, Finance) than SMB, and Mailchimp's brand doesn't shortcut those conversations like Salesforce's does.

• Org is still maturing: You report to a leader building this from scratch. Comp plans might change, territories might shift, and there's startup-level ambiguity despite being inside Intuit.

What Success Looks Like

• Your team hits 90%+ of quota two quarters in a row
• You develop 2-3 reps who get promoted or recruited away (proof you're a talent builder)
• You establish a repeatable playbook for mid-market that other teams adopt
• Your forecast accuracy is within 10% every quarter (leadership trusts your commits)

Who Your Team is Selling To

Primary Buyers:

• VP/Director of Marketing (mid-market companies with 500-2,000 employees)
• Head of Growth or Revenue Ops (fast-growing companies, often e-commerce or DTC)
• CMO (on larger deals, $150K+ ACV)

What They Care About:

• Unifying marketing data across channels (email, SMS, social, ads)
• Ease of use and speed to launch campaigns (they've been burned by complex platforms)
• AI-driven personalization and automation to do more with small teams
• Integrations with their existing stack (Shopify, WooCommerce, Salesforce, etc.)
• Cost compared to HubSpot or Salesforce Marketing Cloud

Requirements

• 3-5+ years managing B2B SaaS sales teams, preferably in martech or sales tech
• Experience selling $50K-$200K+ ACV deals into mid-market (you know this motion cold)
• Proven track record developing reps - you've coached people to quota attainment or promotions
• Comfortable with ambiguity and building processes from scratch (this isn't a defined playbook role)
• Deep martech knowledge - you understand the competitive landscape and can speak to marketing workflows, attribution, and automation
• Based in NYC and willing to be in-office (this isn't a remote role despite Mailchimp's remote culture historically)
• Strong forecasting and pipeline management discipline (Fortune 500 cadence despite startup speed)