Willie Osborn

SDR Manager

Watershed

sales_managerOutbound HeavyEnterprise📍 San Francisco
Deal Size: Team supports AEs closing $200K-$1M+ ACV deals
Sales Cycle: SDRs book meetings; AE cycles are 4-8 months
Posted by Willie Osborn•

Overview

You manage Watershed's SDR team in San Francisco, coaching reps who are prospecting into Fortune 500 companies, major banks, and large enterprises to book qualified meetings for the AE team. Watershed sells a sustainability data and AI platform that helps companies measure, report, and act on climate data—think carbon accounting, ESG reporting, and decarbonization planning. Your team is calling on sustainability directors, CFOs, and chief sustainability officers at companies that need to comply with new climate disclosure regulations or hit net-zero commitments.


Role Snapshot

AspectDetails
Role TypeFrontline Sales Manager (SDR Team)
Sales MotionOutbound-heavy with some inbound from content/events
Deal ComplexityEnterprise—long cycles, multiple stakeholders, regulatory drivers
Sales CycleSDRs book meetings; AE cycles are 4-8 months
Deal SizeAEs close $200K-$1M+ ACV deals
Quota (est.)Team quota: ~40-60 qualified meetings per month across 4-6 SDRs

Company Context

Stage: Series C+ (backed by Sequoia, Kleiner Perkins; high-profile board with John Doerr and Pat Grady)

Size: ~600 employees

Growth: Post says "year of high growth" and expanding sales leadership—they're scaling fast

Market Position: Category creator in sustainability AI. Competing against legacy carbon accounting tools, newer climate tech startups, and internal spreadsheets. They're positioning as the enterprise-grade platform with AI capabilities.


GTM Reality

Pipeline Sources:

  • 60-70% Outbound: Your SDRs are doing cold outreach to named accounts. Lists come from companies with public net-zero commitments, recent climate-related press, or regulatory requirements (public companies, banks under climate stress testing).
  • 20-30% Inbound: Marketing generates leads from content (whitepapers on climate disclosure regs), webinars, and events. Quality varies—some hand-raisers are ready to talk, others are tire-kickers doing early research.
  • 10% Referrals/Partnerships: Some leads come from consulting firms (Big 4) that recommend Watershed to their clients.

SDR/AE Structure: Dedicated SDRs feeding dedicated AEs. SDRs book the meeting, AEs take discovery and run the deal. Clean handoff process.

SE Support: AEs have Solution Engineers for demos and technical validation. SDRs don't do demos—they qualify and hand off.


Competitive Landscape

Main Competitors: Legacy players like Envizi/IBM, newer platforms like Persefoni and Sweep, plus consulting firms building custom solutions and companies trying to DIY with spreadsheets.

How They Differentiate: Watershed pitches AI-powered insights, a flexible platform, and strong methodology (they contribute to industry standards). They're selling to sophisticated buyers who care about data accuracy and auditability.

Common Objections:

  • "We're already tracking this in Excel" or "Our ERP handles it"
  • "We're waiting to see what regulations require"
  • "We just started with [competitor]"
  • Price (enterprise software is expensive)

Win Themes: Data quality, AI capabilities, platform flexibility, customer logos (Walmart, Stripe, Spotify), and ability to handle complex global reporting requirements.


What You'll Actually Do

Time Breakdown

Coaching/1-on-1s (35%) | Pipeline Reviews (25%) | Hiring/Onboarding (20%) | Strategy/Ops (20%)

Key Activities

  • Coach reps through complex prospecting: You're listening to cold calls, reviewing email sequences, and helping SDRs figure out how to get past gatekeepers to reach sustainability directors or finance execs. This isn't transactional SMB prospecting—these are enterprise accounts where it takes 15+ touches to get a response.

  • Run daily/weekly pipeline reviews: You track metrics obsessively—calls made, emails sent, connects, meetings booked, meeting show rate, qualified meeting rate. You're pushing reps to hit activity targets (50-70 calls/day, 100+ emails) and diagnosing why some reps are converting at 2% and others at 5%.

  • Hire and ramp new SDRs: After a high-growth year, you're likely hiring 2-4 more reps in the next 6 months. You source candidates, run interviews, design onboarding, and get new hires productive fast. First 90 days are critical—you're teaching them the product, the buyer personas, and the talk tracks.

  • Work with marketing and AEs on messaging: Sustainability is a newer category, so messaging matters. You collaborate with marketing on what resonates (regulatory compliance vs cost savings vs ESG goals), refine ICPs (which industries/company sizes convert best), and sync with AEs on lead quality and handoff process.

  • Report up to leadership: You're presenting team metrics to the VP of Sales or CRO. They want to know: Are we hitting meeting quotas? What's our cost per meeting? What's the SDR-to-AE conversion rate? Where are bottlenecks?


The Honest Reality

What's Hard

  • It's a new category: Sustainability isn't like selling CRM or HR software where everyone knows they need it. You're often educating prospects on why they should care now, which means more "not interested" and "circle back in 6 months" than you'd get in a mature category.

  • Enterprise outbound is a grind: Getting meetings with Fortune 500 sustainability directors or CFOs is hard. Low connect rates, lots of gatekeeping, and deals that take months even after SDRs hand off. Your reps will get discouraged when they make 300 dials and book 2 meetings.

  • Managing burnout: SDR work is repetitive and rejection-heavy. After 12-18 months, your best reps will want to promote into AE roles. You're constantly hiring and ramping replacements.

  • Balancing quantity and quality: Leadership wants more meetings, but AEs complain if the meetings aren't qualified. You're caught in the middle, pushing for both high activity and high standards.

What Success Looks Like

  • Your team consistently books 40-60 qualified meetings per month that AEs actually want (90%+ show rate, 50%+ convert to opportunities)
  • Reps hit ramp targets (first meeting booked in 30 days, quota in 90 days)
  • Top performers promote to AE within 12-18 months (proves your coaching works)
  • You build repeatable processes so new reps can succeed without needing you to hold their hand

Who You're Hiring and Managing

Your SDR Team:

  • 4-6 SDRs (likely growing to 8-10 by end of year)
  • Mix of experience levels: Some are career SDRs (2-3 years in role), others are recent grads or career switchers hungry to break into tech sales
  • You're coaching them through enterprise prospecting—more complex than SMB SDR work

What They're Measured On:

  • Activity: 50-70 calls/day, 100-150 emails/day (enterprise outbound requires volume)
  • Meetings booked: 8-12 per month per rep (lower than transactional SDR work because these are harder accounts)
  • Qualified meeting rate: 50%+ of meetings convert to opportunities when AEs take them
  • Show rate: 90%+ of booked meetings actually happen

Who Your Team Is Selling To

Primary Buyers (for SDRs to reach):

  • Chief Sustainability Officers or VP/Directors of Sustainability at large enterprises
  • CFOs or finance leaders at public companies dealing with climate disclosure regs
  • ESG/CSR team leads at banks, PE firms, and multinational corporations

What They Care About:

  • Regulatory compliance (SEC climate disclosure rules, EU CSRD, etc.)—this is a big driver
  • Investor/stakeholder pressure to report and reduce emissions
  • Operational efficiency (finding cost savings hidden in sustainability data)
  • Avoiding greenwashing risk—they need defensible, auditable data
  • Simplifying a complex, manual process (most are drowning in spreadsheets)

Requirements

  • 2-3+ years managing an SDR team (preferably in enterprise B2B, not SMB transactional)
  • You've coached reps through complex, multi-touch outbound prospecting (not just dialing for dollars)
  • Experience hiring, onboarding, and ramping SDRs at a growing company
  • Comfortable with metrics and pipeline management—you live in Salesforce and Outreach/Salesloft
  • Belief in the mission matters here—this is climate tech, and they want people who care about the problem they're solving
  • SF-based (they want you in-office to work closely with the sales team)