MSP Mega SKO 2023 (Event Summary)

The Craft of Customer Love: How Kyle Porter Took Salesloft From Overlooked Champion To Category Leader

• We create our own luck.
• The less layers of abstraction between your solution and making money (ROI), the better.
• When you know your solution will help, you become an evangelical seller who can transfer their belief.
• Saleslove sits at the heart of Salesloft.

Scalin’ Up Sales Development: SDR Management For Rapidly Growing Orgs

• Phone is the best channel for cold outbound. LI video and voicemail are also effective. – Gil Abramov
• Before going in cold, spend time working to see if you get a warm intro. – Ralph Barsi
• Execs will weed you out quickly if/when they detect that you are not a trusted advisor.
• The SDR leaders in this session only look at activity if reps are underperforming.
• KPIs:
  • Net contacts added
  • Cadence/sequence completion
• When hiring, seek ‘resourcefulness’ as a trait; this goes along with perseverance
• Many SDR leaders are having their reps fill out & send weekly updates to share KPIs. This drive accountability and self-awareness as well as recognition.

Cutting Edge Sales Tech: Breaking Through the Noise

• 3×3 personalization: one thing about individual, company, industry

Masterclass: Which GTM “Best” Practices are Actually Best?

(Full presentation PDF)

It’s A Balancing Act: Sales Leadership For A Scaling Org…In A Recession

• When adding to your ICP, understand who is organically coming inbound that you are not explicityly targeting
• It may be more effective to measure enablement on one or two granular KPIs (ex: top of funnel conversion) than general productivity. [JD: For any metric you are trying to optimize, think hard about how the metric can be gamed in a way to does damage. For example, increasing ToFu conversion can lead to lower win rates; hence, one must optimize both simultaneously.]
• Compensation for:
  • Sales Engineers: Commission-based with quota tied to the rep(s)/team(s) they support
  • RevOps: Commission-based with same quota as CRO
  • Sales Enablement: Bonus-based with MBOs tied to success on measurable initiatives
• If you are not expanding, you are probably at risk of churn. – Chris Calkin, VP of Revenue, Census

Fireside Chat With PLG Expert Francis Brero, MadKudu’s Founder

• False positives and false negatives deeply damage AI/ML-tool adoption, esp. when the feature (ex: lead scoring) is a ‘black box.’ You not only need a ‘glass box’ but also need a feedback mechanism to pass these ‘errors’ back for tuning the model.
• One score to rule them all is a mistake – for example a score that combines fit (firmographic/demographic) with engagement (behavioral). You need both on the background.
• PQLs have lower conversion rates than high quality inbound MQLs (i.e. demo requests).
• When hiring early sales leaders, hire people who are strongly opinionated about how to sell
• Help the VC partners you are engaged with write the memo they will use to pitch you to their investment committee
• Beware of interested people that have no influence and no authority (NINA – source)
• When selling against an incumbent competitor, create content focused on migration. (example)
• Compensation is trickly in PLG. Reps fear cannibalization and may push to hard to land too large in a way that lowers win rate. This can be solved by given reps ownership for an extended duration (es: 1 year in SMB and indefinite in ENT). Comp reps on anything in their patch regardless of how customers buy.
• In 2023, land smaller to get past CFO resistance.

Taming The Chaos: Leading RevOps At Massive Scale

• Be thoughtful about how changes in one function – sales, marketing, or customer success – impacts that other functions. This is as much if not more mindset as it is reporting structure.
• Put as much if not more energy into manager & rep analysis as you do into executive level reporting.
• As of early 2023, it remains extremely difficult to hire data scientists.
• Focus energy on earning (and re-earning) trust-based value added relationships with sales leader. Meet regularly to understand their business and to deliver proactive insights.
• Periodically meet with reps. Some ideas: office hours or a monthly roundtable.

Grow Up & Glow Up: Scaling Your Sales Team With Turbulence

• Ideally, your first sales hire should have been a first sales hire before
• Key talent metric: time to hire
• Spend time on win-loss analysis
• Build relationships now with great off-the-market talent so they come to when ready to make a move

Selling Sales Tech: How To Sell When You’re Your Own ICP

• In the current market, you may need to disqualify faster. There has to be a strong business case attached to every purchase.
• The buying experience is a direct preview of the customer experience.
• Salespeople have empathy when buying from other sellers
• Potential champions are identified; actual champions are cultivated – Keith Cordeiro
• Just because someone is a champion now does not mean they will be 2 weeks from now; you must constantly invest in them.
• Just because you have a champion does not mean your competitor may not have a stronger champion.

Masterclass: How Buyer Behavior is Changing and What That Means for Sellers

Pipeline Picassos: SDR Leadership In The Enterprise

• Interview question: Tell me about a time when you sacrificed your success for the greater good of the company?
• SDRs need more dedicated enablement than any other role. For example, Snowflake has a 4 week intensive onboarding program for new hires.
• SDRs should regularly be listening to best/worst SDR calls; best/worst AE calls
• The most critical coaching naturally comes from the AEs they are paired with
• If an AE does not partner well with SDRs, then they should lose SDR coverage (for a period)

Sales Leadership in an Efficiency First World

• For better or worse, the sales leaders on this call did not focus on seller certification other than for demoing
• You must find identified pain (the “I” in MEDDPICC) that helps the buyer make money, lower cost, or reduce risk
• Track MEDDPICC score for each deal
• Companies are keeping a closer eye on their ICP to improve efficiency
• Clearly define expectations of ‘what is good’ for each role. Measure the outcomes but not don’t micro-manage how they get there.
• Caring is competence
• Map customer verifiable outcomes to each stage of the sales process

Go For Growth: How David Cancel Took Conversational Sales & Marketing Tech By Storm With Drift

• Build for real-time, not batch processing. This applies not only to tech & data but also to prospect interaction. For example, Drift focuses on real-time qualification and lead routing.
• Engineers are much more likely to fix issues they hear directly from users than via fellow associates
• In Marketing ,Product, etc., be comfortable doing things that don’t scale (Free eBook from Drift – they require email to download). This accelerates learning and builds connection with your community. Things that scale provide limited leverage because everyone is doing them.
• Even if you are freemium, you may want a small sales team just to accelerate learning on what is working and not working observationally.

A Perfect Pairing: How Product and Sales Partners to Drive Product Innovation

• Salespeople should either include product people in meeting with customers or share call recordings
• It is a lot more useful to understand the pain in completing jobs to be done (JTBD) than to ask people for solutions
• Data helps with incremental innovation however data can be over-used in when exploring what needs to be created for two to three years from now.
• Raw feedback from sellers need to be (a) synthesized (b) prioritized relative to company strategy (c) accompanied with stories of specific customer pain

Fireside Chat with Sales Coach, Author, and Entrepreneur Extraordinaire, Cory Bray

• Coaching: Diagnose, Prioritize, Coach, Hold Accountable, Iterate

Can’t Live With ‘Em, Can’t Live Without ‘Em: VC Operating Partners On Creating GTM Excellence

• In 2023, sales training and rep retention is the new hiring
• Reps needs to have deeper 1st conversations and cannot just “do discovery”
• Take the time to assess the skill & diversity gaps on your existing team
• When transitioning from founder-led sales, hire a rep before you hire a VP
• In early 2023, rep comp expectations are still very high
• VCs help in crafting the ideal rep profile and the related interview guide
• Outbound BDR’ing is broken right now and a big reason is that incentives are tied to getting the 1st meeting with a person at an account. Instead, BDRs should focus on helping AEs engage all the buyers in an account. This might mean changing BDRs to salaried associates.
• It does not make sense to have (junior) SDRs choosing which are the best accounts to prospect.
• Take your time to build a library of customer-centric (not marketing-centric) customer stories. Train new hires on these stories with as much if not more emphasis as on product training.
• CSMs need to train customers to sell your renewal to their CFO.

Enable En Masse: Empowering Sales Managers At Large Orgs

• Tracking AIR = activities, indictors, and results
• Strive to hire enablement people who have sales experience
• Ensure buy-in from your CEO, CRO, and CFO to your enablement charter
• Part of the job of sales enablement is to keep distractions away from sellers
• Enablement can serve as a trusted, discrete advisor to new leaders fear asking ‘dumb’ questions
• Buyers are afraid to make mistakes (reference: The Jolt Effect book)
• Focus on manager enablement first including management soft skills, general sales leadership skills, and company specific knowledge/skills
• You’ll get more out of spending time with top performers than with low performers
• Enablement does not need to be part of RevOps but there should at least be very close alignment

Servant Leadership for Sales Ops: Empowering Modern Sales Orgs with Data

• SDR leading indicator(s): new accounts touched in trailing x weeks (or months)
• Monitor for trends in KPIs
• Rev Ops should provide managers with goals using benchmarks, historical performance, and ‘reverse funnel math’
• Things that are low-leverage for Rev Ops (since these are the jobs of sales managers):
  • Riding along on calls
  • Helping reps close individual deals
  • Listening to call recordings
  • Participating in deal reviews
• Pipeline review vs Deal review
  • Pipeline review: High level inspection of close dates; amounts; stage/forecast category
  • Deal review: Deep inspection of deal health (usually using a framework like MEDDPICC)

Change My Mind: Manager Enablement > Rep Enablement

• Manager competencies mentioned
  • Hiring
  • Coaching & developing reps; performance management
  • Alignment with company values
  • Deal reviews & forecasting
  • Territory planning
  • Account Planning
• Set up a scorecard for conversation intelligence call recording reviews
• Sellers need analytics training to be better able to quantify ROI
• Enabling reps is not the sole responsibility of enablement; build a culture of continuous learning across sales leadership

So You Wanna Start a Software Company…

• Go find a cofounder before you do anything else (hacker + hustler)
• Obsess over end-user daily use; obsess over what customers view as quality (ex: data accuracy)

Fireside Chat with Kelly Breslin Wright, Previously COO & President @ Gong

(no major GTM takeaways)

Navigating Stormy Waters for Pre-Public Sales Orgs

• You should be able to look out 18 months and understand the waves of revenue you expect from your strategy – Act A, Act B, and Act C.
• Aim to beat your quarterly target by 5% to 10%. (Note: Your target and your forecast are two different things.)
• Greenhouse forecasting goal: +/-10% at Day 90 and +/-5% at Day 60.
• QBRs (internal) are critical for forecast accuracy
• As you are scaling, make sure you have territories ready for new reps
• RAPID for cross-functional teams: Recommendation; Agreement; Perform; Input; Decision
• If people are not disagreeing in your meetings, you have a dysfunction (ref: 5 Dysfunctions of a Team by Patrick Lencioni)
• Gainsight has a KPI that each executive must speak with a certain number of customers per quarter
• Ryan Bott – ‘Salespeople are not great at telling you what new products to build.’

SaaStr’s Success Story With Founder And CEO, Jason Lemkin

• SaaStr content is heavily focused on ‘how to avoid mistakes’
• To come up with a new SaaS company idea, just ask, ‘What processes have not been SaaS-ified’
• We are currently (in early 2023) in less of a downturn and more of a deceleration. We collectively hired 2x in the last year and paid more (too much) for the people we hired.
• Product, sales, and marketing will each consume 33% of each dollar. To profit maximize, you need to over-index on 2 of the 3 and ‘go to 0’ on the third.
• Jason Lemkin had a rule that he would do one blog post and one Quora answer per day

Fireside Chat with Mark Roberge, Founder @ Stage 2 Capital, Founding CRO @ Hubspot

• Fall in love with the problem, don’t fall in love with the solution
• Early on in a new venture, focus on customer value creation more than on top line value
• High retention is as much if not more dependent on expectation setting by sales as it is on product and customer success (i.e. onboarding & engagement)
• Consider paying AEs 50% on signature and 50% on achieving the first measurable ‘north star’ indicator of retention. For example, when the customer has used 5 features.
• The best sales hire depends on context – what stage are you at and who are you selling to?
• “The Science of Scaling” (content)
• Starting your company with consumption-based pricing is great because it puts the risk on the company.

Get Groovin’: How Chris Rothstein Took Sales Engagement To New Heights With Groove

(no major GTM takeaways)