Exhibit 99.1

S T R I C T L Y P R I V A T E A N D C O N F I D E N T I A L S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 D r a f t - S u b j e c t t o M a t e r i a l R e v i s i o n Project Speed Discussion Materials May 2023

2 Table of Contents 1. Situation Overview 2. Optimization of Omnichannel Retail Business 3. Court Orchestrated Wind - Down 4. Conclusions D r a f t - S u b j e c t S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 t o M a t e r i a l R e v i s i o n

S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 t o M a t e r i a l R e v i s i o n D r a f t - S u b j e c t 1. Situation Overview

4 S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 D r a f t - S u b j e c t t o M a t e r i a l R e v i s i o n Situation Overview M&A / Alternative Outreach: ▪ In the month of April 2022, Shift Technologies, Inc.’s (“Shift” or the “Company”) management began working with Centerview Partners and Cohen & Company (the “Bankers”) to assist it in exploring a sale that would maximize value for the Company ▪ Shift launched a marketing process for a potential sale of the Company ▪ The Bankers ran a robust and active sale process: – Contacted 23 groups of potential financial and strategic investors who are experienced in investing in the automotive & technology sectors, operational turnarounds and/or distressed situations – Solicited interest from approximately 8 potential investors, who had executed nondisclosure agreements (“NDAs”) ▪ In December 2022, Shift completed its merger with CarLotz, which provided additional liquidity to the Company ▪ Furthermore, throughout Q2 2023, Shift independently explored various strategic options, including being acquired, mergers, and asset sales, with ~5 inbound parties Conclusion: ▪ All processes around a sale of the business, selling assets of the business or other type of arrangement concluded on May 26, 2023 with no viable indications of interest ▪ As a result, the Company has pivoted to a standalone plan and is in the process of optimizing the omnichannel retail business and launching the Marketplace

S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 t o M a t e r i a l R e v i s i o n D r a f t - S u b j e c t 2. Optimization of Omnichannel Retail Business

6 S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 D r a f t - S u b j e c t t o M a t e r i a l R e v i s i o n Optimization of Omnichannel Retail Business ▪ Shift will continue to optimize its omnichannel retail business by driving volume and GPU growth, while leveraging its selling, marketing and G&A costs ▪ The Company will do so by further localizing its sales, customer support and F&I teams, to decrease customer handoffs, improve the overall customer experience and sales conversion and eliminate costs for remote support staff ▪ The Company will seek to drive GPU growth, specifically back - end margin, through continuous F&I training for its salespeople and the addition of new lenders and/or products to enhance its F&I offerings ▪ Shift will make further G&A optimizations in order to preserve liquidity throughout the second half of 2023 ▪ Simultaneously, the Company announced plans during its Q1’23 earnings call to continue building the dealer marketplace platform, with an expected soft launch date in Q3, and unit contributions beginning at the beginning of Q4 ▪ The Company will need to raise significant additional capital to meet the liquidity needs of the business going forward; the quantum of capital needed will depend on a number of variables but could range from $100MM to $150MM+ Source: Company provided forecast.

7 D r a f t - S u b j e c t S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 t o M a t e r i a l R e v i s i o n 2023 Dec - 23 Nov - 23 Oct - 23 Sep - 23 Aug - 23 Jul - 23 Jun - 23 May - 23 Apr - 23 Mar - 23 Feb - 23 Jan - 23 $ 109,831 $ (7,345) $ 4,047 $ 12,391 $ 20,173 $ 27,002 $ 34,077 $ 35,409 $ 45,100 $ 67,721 $ 77,432 $ 87,484 $ 109,831 Cash BOP (74,983) (4,901) (4,965) (5,036) (5,013) (4,893) (5,214) (6,303) (6,967) (6,865) (7,702) (7,395) (9,730) EBITDA (5,596) (422) (422) (422) (422) (422) (422) (349) (349) (349) (501) (583) (931) CapEx (Tech) (5,764) 569 272 (812) 172 (853) (787) 11,483 (2,144) (11,513) 4,463 (556) (6,059) Working Capital (7,458) (450) (500) (550) (600) (650) (700) (500) (550) (550) (780) (788) (840) Ongoing Leases (10,026) (472) (3,676) (174) (469) (161) (152) (3,863) (81) (179) (466) (153) (179) Interest on Debt (18,874) 150 (2,100) (1,350) (1,450) 150 200 (1,800) 400 (3,166) (4,725) (577) (4,607) Other $ (12,871) $ (12,871) $ (7,345) $ 4,047 $ 12,391 $ 20,173 $ 27,002 $ 34,077 $ 35,409 $ 45,100 $ 67,721 $ 77,432 $ 87,484 Cash EOP Cash Gain/(Use) (22,346) (10,052) (9,711) (22,621) (9,691) (1,332) (7,075) (6,829) (7,782) (8,344) (11,392) (5,526) (122,702) Source: Company provided forecast. (1) Cash flow forecast assumes cost savings from omnichannel retail optimization that have been identified but not yet implemented 2023 Cash Flow Analysis ($ in Thousands) 2023 Cash Flow (1)

S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 t o M a t e r i a l R e v i s i o n D r a f t - S u b j e c t 3. Court Orchestrated Wind - Down

9 S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 D r a f t - S u b j e c t t o M a t e r i a l R e v i s i o n Court Orchestrated Orderly Liquidation Analysis ▪ Model assumes a liquidation plan starting on October 31, 2023 – Liquidation analysis based on Company - projected cash flow and asset values, as of May 2023 – Assumed Chapter 11 liquidating plan – Assumed vehicles are sold through omnichannel retail for 3 - 5 months – any unsold vehicles are assumed to be sold to auction house ▪ Analysis is based on actual April 30, 2023 balance sheet, with the following adjustments: – Cash, Inventory, Ally Debt has been rolled forward based on the projections provided by the Company – Trade credit is assumed to tighten as awareness of further liquidity constraints increases ▪ Analysis has been done on a consolidated basis vs legal entity level ▪ Secured Debt Ally – Assumed to be paid 100% in all cases, due to vehicle level security ▪ Based on industry standard recovery rates the estimated recovery to the unsecured creditors, including the holders of the Senior Convertible Notes would recover 0% Source: Company provided forecast.

10 D r a f t - S u b j e c t S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 t o M a t e r i a l R e v i s i o n Recovery Recovery FCST $ % 10/31/23 $ 4,047 100.0% $ 4,047 Asset Value Cash 3,708 70.0% 5,297 Accounts receivable, net 26,863 82.0% 32,760 Inventory 145 2.5% 5,782 Prepaid and other current assets 308 7.5% 4,113 Property and equipment, net 635 6.5% 9,763 Capitalized website /software 29 1.5% 1,933 Other non - current assets $ 35,735 56.1% $ 63,695 Net Proceeds from Assets $ 21,294 $ 21,294 Secured Debt Ally - Floor Plan 100.0% Recovery % $ 14,440 Amount Available to Estate $ 450 Administrative Costs US Trustee Fees 5,250 Wind - Down Budget 10,000 Professional Fees 2,000 503(b)(9) Claims 1,000 Employee Claims $ 18,700 Administrative Costs $ (4,260) Amount Available to Unsecured Claims - $ 8,400 Unsecured Claims AP Trade - 13,100 Other Accrued - 8,000 Lease Rejection Claim - 20,200 Senior Unsecured Notes - 153,100 Convertible Notes - 5,000 Litigation Claims - 0.0% $ 207,800 Unsecured Claims Recovery % Source: Company provided forecast. Liquidation Analysis ($ in Thousands) Project Speed – Orderly Liquidation Analysis

S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 t o M a t e r i a l R e v i s i o n D r a f t - S u b j e c t 4. Conclusions

12 S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 D r a f t - S u b j e c t t o M a t e r i a l R e v i s i o n Conclusions ▪ For the past 16 months, the Company has engaged multiple advisors and run multiple processes to fundraise or pursue M&A with no success, in large part due to the significant debt burden on the Company ▪ The Company has a go forward plan that has execution risk and will require additional money ▪ Alternatives are limited in light of the industry and historical performance

13 S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 D r a f t - S u b j e c t t o M a t e r i a l R e v i s i o n DISCLAIMER THIS DOCUMENT IS FOR DISCUSSION PURPOSES ONLY AND DOES NOT CONSTITUTE ADVICE OF ANY KIND, INCLUDING TAX, ACCOUNTING, LEGAL OR REGULATORY ADVICE, AND OPPENHEIMER & CO . INC . IS NOT AND DOES NOT HOLD ITSELF OUT TO BE AN ADVISOR AS TO TAX, ACCOUNTING, LEGAL OR REGULATORY MATTERS . THIS DOCUMENT WAS PREPARED ON A CONFIDENTIAL BASIS SOLELY FOR DISCUSSION BY THE COMPANY AND OPPENHEIMER & CO . INC . AND NOT WITH A VIEW TOWARD PUBLIC DISCLOSURE . THIS DOCUMENT SHALL BE TREATED AS CONFIDENTIAL BY ITS RECIPIENTS . THE INFORMATION CONTAINED HEREIN WAS OBTAINED FROM THE COMPANY AND PUBLIC SOURCES AND WAS RELIED UPON BY OPPENHEIMER & CO . INC . WITHOUT ASSUMING RESPONSIBILITY FOR INDEPENDENT VERIFICATION AS TO THE ACCURACY OR COMPLETENESS OF SUCH INFORMATION . ANY ESTIMATES AND PROJECTIONS FOR THE COMPANY CONTAINED HEREIN HAVE BEEN SUPPLIED BY THE MANAGEMENT OF THE COMPANY OR ARE PUBLICLY AVAILABLE, AND INVOLVE NUMEROUS AND SIGNIFICANT SUBJECTIVE DETERMINATIONS, WHICH MAY NOT BE CORRECT . NO REPRESENTATION OR WARRANTY, EXPRESS OR IMPLIED, IS MADE AS TO THE ACCURACY OR COMPLETENESS OF SUCH INFORMATION AND NOTHING CONTAINED HEREIN IS, OR SHALL BE RELIED UPON AS, A REPRESENTATION OR WARRANTY, WHETHER AS TO THE PAST OR THE FUTURE . THE INFORMATION CONTAINED HEREIN WAS DESIGNED FOR USE BY SPECIFIC PERSONS FAMILIAR WITH THE BUSINESS AND AFFAIRS OF THE COMPANY AND OPPENHEIMER & CO . INC . ASSUMES NO OBLIGATION TO UPDATE OR OTHERWISE REVISE THESE MATERIALS . OPPENHEIMER & CO . INC . ’S RESEARCH DEPARTMENT IS REQUIRED TO BE INDEPENDENT FROM ITS INVESTMENT BANKING DEPARTMENT, AND ITS RESEARCH ANALYSTS MAY HOLD AND MAKE STATEMENTS OR INVESTMENT RECOMMENDATIONS WITH RESPECT TO THE COMPANY AND/OR ANY OFFERING CONDUCTED BY THE COMPANY THAT DIFFER FROM THE VIEWS OF ITS INVESTMENT BANKERS . FURTHER, PURSUANT TO APPLICABLE LAW OPPENHEIMER & CO . INC . IS (AMONG OTHER THINGS) PRECLUDED FROM OFFERING FAVORABLE RESEARCH, A SPECIFIC RATING OR A SPECIFIC PRICE TARGET, OR THREATEN TO CHANGE RESEARCH, A RATING OR A PRICE TARGET, TO THE COMPANY AS CONSIDERATION OR INDUCEMENT FOR THE RECEIPT OF BUSINESS OR COMPENSATION .

14 S t r i c t l y C o n f i d e n t i a l S u b j e c t t o F R E 4 0 8 D r a f t - S u b j e c t t o M a t e r i a l R e v i s i o n FORWARD LOOKING STATEMENTS THIS DOCUMENT INCLUDES “FORWARD LOOKING STATEMENTS” WITHIN THE MEANING OF THE “SAFE HARBOR” PROVISIONS OF THE UNITED STATES PRIVATE SECURITIES LITIGATION REFORM ACT OF 1995. FORWARD - LOOKING STATEMENTS MAY BE IDENTIFIED BY THE USE OF WORDS SUCH AS “FORECAST,” “INTEND,” “SEEK,” “TARGET,” “ANTICIPATE,” “BELIEVE,” “EXPECT,” “ESTIMATE,” “PLAN,” “OUTLOOK,” AND “PROJECT” AND OTHER SIMILAR EXPRESSIONS THAT PREDICT OR INDICATE FUTURE EVENTS OR TRENDS OR THAT ARE NOT STATEMENTS OF HISTORICAL MATTERS. SUCH FORWARD LOOKING STATEMENTS INCLUDE ESTIMATED FINANCIAL INFORMATION. SUCH FORWARD LOOKING STATEMENTS WITH RESPECT TO REVENUES, EARNINGS, PERFORMANCE, STRATEGIES, PROSPECTS AND OTHER ASPECTS OF SHIFT’S BUSINESS ARE BASED ON CURRENT EXPECTATIONS THAT ARE SUBJECT TO RISKS AND UNCERTAINTIES. A NUMBER OF FACTORS COULD CAUSE ACTUAL RESULTS OR OUTCOMES TO DIFFER MATERIALLY FROM THOSE INDICATED BY SUCH FORWARD LOOKING STATEMENTS. THESE FACTORS INCLUDE, BUT ARE NOT LIMITED TO: (1) SHIFT’S ABILITY TO GROW AND MANAGE GROWTH PROFITABLY, MAINTAIN RELATIONSHIPS WITH CUSTOMERS AND SUPPLIERS AND RETAIN ITS MANAGEMENT AND KEY EMPLOYEES; (2) CHANGES IN APPLICABLE LAWS OR REGULATIONS; (3) THE POSSIBILITY THAT SHIFT MAY BE ADVERSELY AFFECTED BY OTHER ECONOMIC, BUSINESS, AND/OR COMPETITIVE FACTORS; (4) THE OPERATIONAL AND FINANCIAL OUTLOOK OF SHIFT; (5) THE ABILITY FOR SHIFT TO EXECUTE ITS STRATEGY; (6) SHIFT’S ABILITY TO PURCHASE SUFFICIENT QUANTITIES OF VEHICLES AT ATTRACTIVE PRICES; (7) LEGISLATIVE, REGULATORY AND ECONOMIC DEVELOPMENTS AND (8) OTHER RISKS AND UNCERTAINTIES INDICATED FROM TIME TO TIME IN OTHER DOCUMENTS FILED OR TO BE FILED WITH THE SEC BY SHIFT. YOU ARE CAUTIONED NOT TO PLACE UNDUE RELIANCE UPON ANY FORWARD - LOOKING STATEMENTS, WHICH SPEAK ONLY AS OF THE DATE MADE. SHIFT UNDERTAKES NO COMMITMENT TO UPDATE OR REVISE THE FORWARD - LOOKING STATEMENTS, WHETHER AS A RESULT OF NEW INFORMATION, FUTURE EVENTS OR OTHERWISE, EXCEPT AS MAY BE REQUIRED BY LAW.