Bowery Capital 2019 Sales Summit (Trip Report)

How to Successfully Prepare Your GTM Org to Move Upmarket

• Sales & marketing must be aligned on accounts to coordinate engagement strategy
• Upskill reps (and supporting functions) to successfully execute new processes
• Do an internal "GTM listening tour" to identify what is working and what is not working
• The up-marketing forecasting cadence must change; specifically, you must not only examine current commits but also look at out-of-quarter (top) deals.
• For TAM modeling, speaker recommends DataFox & HG Insights

Tips for Driving and Negotiating Deals to Close

• Warning: Your champion is often not the decision-maker even though they may think they are
• Only negotiate with the true economic buyer (usually the CFO or another finance person).
• So that you don't negotiate against yourself, (a) make sure the deal is not blocked - ex. due to budget issue (b) start by asking the prospect what is most important to them.
• Know whom you are competing against to ensure your proposal is competitive on pricing and terms
• Buyer communities (like MSP for Sales) have made pricing highly transparent -- so be consistent from deal-to-deal.
• Preempt deals from getting stuck by being prescriptive about next steps from the start (in other words, use mutual action plans)
• Ensure you are 'multi-threaded' (engaging with multiple stakeholders) as early as possible on each deal
• Build peer-to-peer executive alignment into your sales process
• Every prospect in a meeting should receive a personalized follow-up
• If a deal is stuck, show up in person (admittedly a bold move)
• Ways to create urgency: (a) exploding price (b) mutual plan with owners & deadlines (c) sharing implementation timing backlog (d) tying to prospect's critical initiative dates
• Some good give-gets: (a) logo use (b) case study (c) testimonial (d) reference
• Strive to get approval on commercial terms and conditions early; once legal has reviewed, you are in the driver's seat on the deal
• Refuse to redline contracts below a certain value. (Yes, this means you need neutral if not prospect-friendly T&Cs.)

Me vs. We: Going from Individual Contributor to Leader

• Key changes: (1) control --> trust (2) consume resources --> create & allocate resources (3) receive recognition --> give recognition and take blame
• Use the Team Lead role to groom talent; this sets up not only the manager but also their team for success
• Signs a person is ready to lead: (1) High competency/achievement (2) sought out by peers for advice (3) positively finds & solves problems (4) not threatened by others' success (5) cares about helping others = empathy
• For team leads to be successful, (a) reduce their quota (b) provide training & support (c) align comp with team performance
• Consider devoting team leads to focus on ramping reps

Building a Modern Sales Organization: Frameworks from 450 Tech Companies

• Determine how your buyers buy THEN build your sales process THEN hire people who are skilled at executing that process
• Key question for reference checks: Would you rehire this person? Importantly, listen for any hesitation (then probe).
• Ask references to do a word association test by choosing ~10 words tied to your core values and have them rate the candidate on each word on a 1 to 5 scale. Probe on anything at or below a 3.
• You must do at least one backchannel reference check (but avoid anyone from the candidate's current employer).
• Hiring managers should do final reference checks, not recruiters.
• When recruiting leaders, ask, "Whom will you recruit to join our team?"
• Exercises: (1) For reps, have them mock pitch your product -- Bonus: They should proactively ask you questions during their prep (2) Leadership: Role play performance management conversations
• To induce enterprise reps to join, offer (a) higher OTE (b) larger territory (c) 3 to 6 month ramp guarantee

Sales Operational Excellence at All Stages of a B2B Startup

• When prioritizing projects, crowd-source from your team but confirm with executive leadership before you execute
• Beware of prioritizing on squeaky wheels and/or shiny objects
• Things RevOps leaders wish they had done sooner: (1) Build and document a stronger data foundation (2) streamline & strictly govern the type & number of fields in CRM (3) Support reps at all phases incl. onboarding, ramp, and ongoing (4) provide random acts of coaching
• Things RevOps leaders felt would matter but didn't after all: (1) Reporting for the sake of reporting rather than reporting only to drive action/decisions (2) Buiding persona decks too early (3) Tweaking CRM fields without definitive business impact (4) Buying sales commission software too early (5) letting perfect get in the way of good enough
• Things RevOps leaders are actively holding off on: (1) Going from single product focused to multi-product sellers (2) Implementing forecasting tools (3) Implementing customer success software (4) Implementing LMS since conversational intelligence serves the need (5) Implementing CPQ since reps struggle with self-service
• Metrics-driven forecasting is hard for (a) small volume (b) large deals (c) long sales cycle. In this case, the only solution is deep deal-by-deal review.

From the Industrial Revolution to the RevOps Revolution

• Universal RevOps equation (aka sales velocity) = (# opps) x (win rate) x (ASP) / (sales cycle days)